Only A True NHL Fan Can Name These 40 Stars Holding The Stanley Cup

Trophies are coveted and revered items in sports. Far from a mere piece of hardware, they are representative of greatness, symbolic signs to recognize the team that reigns supreme atop their sport. And even as measured by that lofty standard, the Stanley Cup stands tall among its fellow celebrated silverware.

For one thing, there’s it’s rich history, with the first Cup being awarded in 1893 after being donated by Lord Stanley of Preston to Canada’s top amateur hockey team. But even apart from a 126-year (and counting) lifespan, the Cup’s aura transcends its longevity. There’s also its classic design and the significance of literally having its history inscribed upon it, with the names of the members of each year’s winning team etched into it. To top it off, you also have the ceremonial element of watching every Finals victor hoist the Cup above their heads in triumph during the immediate aftermath of their championship, not to mention getting their own day with it that summer.

Given the lore and tradition behind the trophy, it must truly mean something to have lifted the Stanley Cup, especially since NHL players who never earned the honour wouldn’t dare touch the hallowed hardware. Even all-time greats like Marcel Dionne and Adam Oates lose some degree of clout for not having a Cup on their resume. Conversely, these legends of the game have ensured that their names will live on in hockey history our through the Cup and their place on it. And surely they have their own Cup-hoisting picture stored away somewhere as a keepsake right along with their Stanley Cup ring.

Question 1

Name this Stanley Cup champion!

Arguably one of the greatest defensemen in NHL history, this Hockey Hall of Fame inductee wasn’t really a high ceiling prospect upon entering the league. In fact, he lasted until the 53rd pick of his 1989 draft year before being claimed. All he did from there was go on to win seven Norris trophies for best blue liner and a Conn Smythe award as the playoff MVP. Most importantly, he won four Stanley Cups, all the while spending the entirety of his 20-year NHL journey with the Detroit Red Wings. The Original Six franchise built a dynasty on the backs of homegrown stars like him.

Question 2

Name this Stanley Cup champion!

The celebrated legacy of this modern NHL mega-star had already been cemented prior to the 2015-16 season, but anchoring the Pittsburgh Penguins to back-to-back Stanley Cup championships in 2016 and 2017 added even more acclaim to an NHL journey that was already Hall of Fame-caliber. Thanks, in part, to his 77 points across three Cup-winning playoff runs, this two-time Hart trophy and Conn Smythe winner has already entered rarefied air among postseason performers. Still only 31 years of age, he has already climbed into the top 10 of playoff scorers all-time. By next season, he could even leap into the top five.

Question 3

Name this Stanley Cup champion!

Before Sidney Crosby and Evgeni Malkin came on board to usher in a new golden era in Pittsburgh, the foundation of a roster that won three Stanley Cups in nine years was already in place. With the first overall pick of the 2003 NHL Draft, the Penguins made this star netminder just the second goaltender to go No. 1 in league history. Over the ensuing three drafts, Malkin, Crosby and Jordan Staal all joined the fold, creating a base for future greatness. Though no longer with the club, this four-time All-Star spent last season backstopping the expansion Vegas Golden Knights all the way to the Stanley Cup Finals.

Question 4

Name this Stanley Cup champion!

Prior to their recent slide down the standings, it felt like the Anaheim Ducks had reigned as a perennial Cup contender forever. So it's a bit odd, then, to think that they have actually only hoisted Lord Stanley’s mug once in their history. That triumph came in 2007, when this hulking defenseman formed half of a Hall of Fame blue line tandem that helped anchor the Ducks. This former Hart and Norris trophy winner had just arrived in Anaheim that season, coming over from Edmonton after leading the Oilers to the 2006 Stanley Cup Finals. Needless to say, he made an immediate impact.

Question 5

Name this Stanley Cup champion!

Long viewed as something of a lowly laughingstock of an organization that was mired in a 49-year Cup drought, the Chicago Blackhawks turned things around thanks, in large part, to their work at the draft table. Chicago made the most of a couple of high back-to-back draft choices in 2006 and 2007, nabbing Jonathan Toews with the third pick of the 2006 draft and then landing this explosive winger with the No. 1 pick in 2007. With those two young, homegrown forwards leading the way, the Blackhawks reeled off three Stanley Cup championships in six years between 2010 and 2015.

Question 6

Name this Stanley Cup champion!

Admittedly, this raising of the Stanley Cup came long after the end of the playing time of this all-time NHL great. But long before he was winning championships as the owner of the Pittsburgh Penguins, he was a gifted forward and a scoring superstar for the franchise. Those playing days produced their own back-to-back Stanley Cups in 1991 and 1992, just as the club did under his watchful eye as owner 25 years later. Some will wonder how many more Cups the three-time Hart Trophy winner might have had Hodgkin’s lymphoma and numerous back surgeries not cost him much of his prime, but five Stanley Cup rings two as a player, three as an executive) isn’t half bad.

Question 7

Name this Stanley Cup champion!

Even the Great One, himself, proved ultimately unable to bring a Stanley Cup to the city of Los Angeles, so it was clearly going to take a special team to bring the Kings their first trophy. With this hard-nosed blueliner leading the way, some recent Kings teams did even better than that, winning two Cups in three seasons between 2012 and 2014. The 2016 Norris Trophy winner reigned as the league’s highest-scoring defenseman during the 2012 playoffs. In 2014, he became just the second player ever to win a Stanley Cup and an Olympic gold medal in the same calendar year.

Question 8

Name this Stanley Cup champion!

Now known mainly for his signature facial hair, this popular forward had a pretty good on-ice journey as well. That 18-year stint culminated with an elusive Stanley Cup as a member of the Calgary Flames in 1989. Then a 36-year-old veteran, the one-time 66-goal scorer decided to go out on top, opting to hang up his skates and retire after finally lifting the Cup. This achievement couldn't have happened to a more deserving person. The former Toronto Maple Leafs remains widely recognized as one of the game's good guys, winning the Bill Masterton and King Clancy trophies, hardware that stands to recognize strong character, perseverance and integrity.

Question 9

Name this Stanley Cup champion!

This bruising Washington Capitals forward carries something of a poor reputation around the league. That's what happens when you've lost 25 games to suspension over the past two seasons. Still, a physical, gritty style of play on the ice doesn't mean that the 25-year-old isn't a good guy off of it. Here, he's pictured sharing the Cup with a young Capitals fan. However you feel about Alex Ovechkin's linemate, it's hard to argue that he wasn't a vital cog in Washington's 2018 title chase, tallying five goals and 15 points in 21 playoff games to help the Caps finally get over the hump.

Question 10

Name this Stanley Cup champion!

If you know anything about hockey, chances are you recognize this young Edmonton Oilers star, who just so happened to go onto become the best player in NHL history. But even as the league's all-time leading scorer was rewriting the record books with gaudy scoring stats year after year, Stanley Cup triumphs proved elusive, especially in the latter parts of "The Great One's" hockey journey. Sure, he won four Cups in five years during the Oilers' dynasty of the 1980's, but while Edmonton would win one more title after "The Trade", number 99 would never again have a chance to raise hockey's holy grail.

Question 11

Name this Stanley Cup champion!

The Stanley Cup has rarely been held as high in the air as it was in 2011 when it was lifted to the sky by this 6'9" Boston Bruins captain. That championship stands as the only one that the fearsome blue liner has attained during a 20-year hockey journey that is still on-going. That season, he was named to his fifth All-Star Game and led the league in plus/minus (+33) before leading the Bruins in average time on ice during the postseason. With Boston still a perennial playoff contender and the 2009 Norris Trophy winner still going strong at age 42, who's to say he can't win another one?

Question 12

Name this Stanley Cup champion!

Goaltenders have always been known to be something of an odd breed, bearing unconventional superstitions, weird habits and routines and curious personality quirks. For this instantly distinguishable netminder, however, that strangeness always existed more on the ice through his unique style of play. Far from the traditional butterfly-style goalies that populate the NHL, this Hall of Famer flopped his way to two Hart trophies, six Vezina awards and two Stanley Cups. Though most of his prime years came with the Buffalo Sabres, he earned both Cups over two separate stints with the Detroit Red Wings – the latter championship coming at age 41.

Question 13

Name this Stanley Cup champion!

Long since remembered as a Hall of Fame talent who saved his best for the postseason, this New York Islander’s early playoff runs actually weren’t particularly kind to him. Even as he won the Calder Trophy for top rookie in 1976, he would struggle in his first four playoff runs, scoring just 27 points in his first 42 postseason games. By comparison, he would record 29 points upon culmination of the regular season in each of the next three years. It’s no coincidence, then, that the sudden spike in playoff performance by the Hall of Fame center happened to align with his Islanders reeling off four consecutive Stanley Cup triumphs.

Question 14

Name this Stanley Cup champion!

By the time this Hall of Fame winger made his way to Tampa Bay as a free agent in July of 2001, he already had 19 NHL seasons under his belt and was well into the twilight of a decorated hockey journey. He had suited up for five other clubs, made two All-Star teams and even surpassed the 50-goal mark on two separate occasions. He’d been around so long, in fact, that the Lightning didn’t even take the ice for their inaugural season until the bruising forward had spent nearly a decade in the league. And so it was fitting that his stint in Tampa, where he earned the captaincy, would bring about a long-awaited Stanley Cup in 2004 for the then-40-year-old.

Question 15

Name this Stanley Cup champion!

You didn’t have to be a fan of the Colorado Avalanche to cheer on the Stanley Cup quest of this legendary defensive stalwart. After spending the first 21 seasons of his hockey journey with the Boston Bruins, the Hall of Fame blueliner was traded to Colorado for a shot at an elusive Cup run. While seeing a player tied so closely to one franchise make a late move can be uncomfortable at times, everyone - Bruins fans included - were rooting for this Hall of Famer, seen here on the left, to finally lift the Cup. That he did it in his 22nd and final NHL season made it all the sweeter.

Question 16

Name this Stanley Cup champion!

Backstopping a club to a Stanley Cup victory requires both being good and being lucky. Of course, it takes some sure-handed work between the pipes to navigate through four grueling rounds of hockey against the best that the NHL has to offer, but there’s also the need to be in the right situation at the right time. After all, no goalie has ever won the Cup by themselves. This long-time Chicago Blackhawks goaltender stands as living proof of this necessary balance. The 34-year-old is certainly no pushover, as his two All-Star appearances would suggest, but he’s never been a serious Vezina candidate and is rarely mentioned among the league’s best at the position. Still, he’s been good enough to man the pipes for two Cup-bound Chicago teams.

Question 17

Name this Stanley Cup champion!

Every championship team needs talent, but they also need a group of hard-working guys who get along with each other. Enter this 18-year NHL veteran, a productive winger, proven leader and three-time Stanley Cup champion. Though he has never really been a superstar-caliber player, he seems to be at his best in the biggest moments. Not only does he have a 2014 Conn Smythe Award to his credit, but he has earned the nickname 'Mr. Game 7' for his seven goals and 14 assists in the seventh and deciding game of playoff series, both of which are still NHL records.

Question 18

Name this Stanley Cup champion!

While they haven't won a championship since 1993, the Montreal Canadiens still reign atop NHL history with 24 Stanley Cup triumphs, by far the most of any franchise. And perhaps no one person stood as a greater embodiment of that rich history than this Habs legend. A lifetime member of the 'bleu, blanc et rouge', this late two-time Hart trophy winner had a hand in 17 of them - 10 as a player and seven as a club executive. Even as part of an organization with such a decorated playoff history, the 1965 Conn Smythe Award winner as their all-time leading postseason scorer.

Question 19

Name this Stanley Cup champion!

Taking place in Vancouver, BC, the upcoming 2019 NHL Entry Draft will see the Chicago Blackhawks face a big decision with their No. 3 overall pick. The last time the 'Hawks held the coveted third pick came back in 2005 during a draft that, coincidentally, also took place in Vancouver. Based on the success of that pick, it stands to reason that Chicago would love to see lightning strike again. That 2005 draft would see the club land this franchise center and long-time captain, who was instrumental in three Cups in six years for an organization that had been mired in a 49-year drought.

Question 20

Name this Stanley Cup champion!

This Hall of Fame center spent the entirety of his 20-year NHL journey in the Quebec Nordiques / Colorado Avalanche organization. Over that time, he rose to the top spot in most statistical categories, establishing himself as arguably the best player in the history of the club. And yet, two years unquestionably stick out. The three-time All-Star led the Avs to Stanley Cup glory in 1996 and 2001 and has his fingerprints all over each of those Cups. In 1996, he scored a league-high 18 playoff goals and 34 points to win the Conn Smythe Award. In 2001, he carried Colorado into the postseason on the strength of a Hart trophy-winning campaign.

Question 21

Name this Stanley Cup champion!

This Hall of Fame blueliner never scored more than 15 goals in a season. However, anyone who watched him serve as a lynchpin for some very good defensive units in New Jersey and Anaheim can attest to the significance of his influence on building a winner. The first two of the four-time All-Star's three Cups came as part of the Devils' stifling back end, while the third saw him earn a Conn Smythe Award by forming an imposing defensive pairing alongside fellow Hall of Famer Chris Pronger on the Ducks' blue line. None of those three Cups would have been possible if not for this mobile rearguard's presence.

Question 22

Name this Stanley Cup champion!

The Washington Capitals' 2018 Stanley Cup triumph carried so many subplots that made the win that much sweeter to hockey fans in the nation's capital. There was the comeback down 2-0 against Columbus, finally conquering the rival Pittsburgh Penguins and the raucous celebrations of Alex Ovechkin. Yet these stories paled in comparison to the emotional impact of seeing this Caps star forward tearfully bask in the moment with his family and, most notably, his father, Tim. His dad had been a sparse presence at Washington games on account of his battle with Alzheimer's disease, but was there to see his son hoist the Cup for the first time.

Question 23

Name this Stanley Cup champion!

The Detroit Red Wings enjoyed a remarkable boom period between the late 1990's and through the 2000's that saw them take home four Stanley Cups in 12 years. That prolonged success would not have been possible without the club's famous knack for landing star-caliber talent late in the draft. Carrying on in the tradition of players like Nick Lidstrom, Sergei Fedorov and Pavel Datsyuk, the Wings nabbed this future superstar 210th overall in 1999. All he did from there was earn Conn Smythe Award honors along the way to leading Detroit to a 2008 Cup victory by scoring 13 goals and 27 points in 22 games.

Question 24

Name this Stanley Cup champion!

A heated 1996 Western Conference Semifinal between the Colorado Avalanche and Chicago Blackhawks saw stars of each team engaged in a verbal back-and-forth. When Blackhawks star forward Jeremy Roenick criticized the play of the Avs' star goaltender, the netminder fired back with, "I can't really hear what Jeremy says, because I've got my two Stanley Cup rings plugging my ears." By the time the long-time Montreal Canadiens star was done, he actually had added two more rings to that tally, a true sign of a legendary journey between the pipes. Boasting an NHL record three Conn Smythe Awards, the league's all-time winningest goalie has had his number retired by both Montreal and Colorado.

Question 25

Name this Stanley Cup champion!

So loaded were the Montreal Canadiens teams of the 1960's and 1970's that it's easy to overlook even some of their Hall of Fame players. This defenseman won seven Stanley Cups while manning the blue line for Habs teams with some all-time great forwards. That's not to say, of course, that this All-Star rearguard wasn't a great player in his own right. In fact, he won the 1969 Conn Smythe Award while playing alongside a roster that also featured Hall of Famers Jean Beliveau, Yvan Cournoyer, Henri Richard and Dick Duff. Though somewhat unheralded, this 17-year veteran was nonetheless vital to those seven Cup winning Habs teams.

Question 26

Name this Stanley Cup champion!

When you command respect in your particular field, you sometimes earn the right to be called "Mister". Gordie Howe was 'Mr. Hockey', Reggie Jackson was 'Mr. October' and this stalwart defenseman was 'Mr. Devil'. Although this unassuming blue liner topped out at six goals in an NHL season, he earned the affection of the New Jersey faithful for spending all 20 seasons of his time in the Swamp, suiting up for a franchise record 1,283 games. It's only fitting, then, that he won three Cups as a core, albeit somewhat overshadowed, member of the Devils' fearsome blue line of the 1990's.

Question 27

Name this Stanley Cup champion!

How impactful was this high-scoring defenseman upon making his debut with the New York Islanders during the 1973-74 season? He took a club that had recorded the fewest points in NHL history one year prior to his arrival and carried them to within one win of the Stanley Cup Finals two years later. From winning the Calder trophy in 1974 to leading the Islanders to four Cups before his 30th birthday, this Hall of Fame blueliner wasted no time making good on his No. 1 overall draft selection. In fact, as soon as the three-time Norris trophy winner earned the captain's "C", it sparked a string of four Cups in a row on Long Island.

Question 28

Name this Stanley Cup champion!

This superstar scorer made headlines last spring when he and his Washington Capitals put years of playoff disappointments behind them and finally earned the right to drink from Lord Stanley’s mug. That, however, was just the beginning for the so-called “Great Eight”. The three-time Hart Trophy winner led the way on a summer-long celebration with new pal Stanley in tow. There were spontaneous public renditions of “We Are the Champions”, partially-clothed forays into fountains and plenty of other endearing antics. If the Caps were to make another run at the Cup, you’d have to wonder what the 2018 Conn Smythe Award winner might do for an encore.

Question 29

Name this Stanley Cup champion!

The names etched upon the Stanley Cup serve to create something of a road map that forms the basis of hockey history. But few of those names tell as unlikely a story as does the name of this standout Boston Bruins goaltender. A journeyman who didn’t become an NHL regular until after his 31st birthday, he transformed into a late-blooming success, winning Vezina trophies at age 34 and 36. That second Vezina campaign in 2010-11 also coincided with backstopping the Bruins to a Stanley Cup championship and even winning a Conn Smythe Award along the way. Though he wasn’t in Boston long enough to stand atop any all-time franchise records, Bruins fans will never forget his role in bringing them their only Cup since 1972.

Question 30

Name this Stanley Cup champion!

Look, it's easy to quickly dismiss this speedy winger's two Stanley Cups as at least somewhat undeserved. After all, thanks to a trade in the summer of 2015, he was joining a team that already featured Sidney Crosby and Evgeni Malkin and had won 11 playoff series, including a Stanley Cup, over their past eight years. Upon closer inspection, however, it's clear that the 2016 and 2017 Cups don't happen in Pittsburgh without the contributions of this three-time All-Star. His 45 points across the two Stanley Cup-winning playoff campaigns is just one point shy of the total production of each of Crosby and Malkin over that same stretch.

Question 31

Name this Stanley Cup champion!

In an era of so much roster turnover and player movement, it's remarkable to still find examples of great players enjoying long NHL journeys with just one team. This decorated leader didn't merely spend his entire time with the Detroit Red Wings, however. He spent an incredible 19 of his 22 seasons as the club's captain. Over that time, all the Red Wings did was win three Stanley Cups and reach the postseason in all but one season. The 1998 Conn Smythe winner now enjoys lofty status among the all-time leaders in the history of the storied franchise, sitting second behind "Mr. Hockey" Gordie Howe on Detroit's all-time goals and points list.

Question 32

Name this Stanley Cup champion!

For all of the individual accolades accumulated by this speedy Finnish winger, he spent much of his time in the NHL saddled with an unwanted reputation as a runner-up. He was the 1993 Calder trophy winner, the recipient of the inaugural Rocket Richard trophy in 1999 and a four-time All-Star, but he consistently fell short when it came to championships. In international play, he amassed silver medals at the Olympics and World Championships, but could never attain gold. At the NHL level, it was only in his 15th season when, after 1,041 games, finally hoisted the Cup as a member of the Anaheim Ducks.

Question 33

Name this Stanley Cup champion!

You might assume that a guy who wins 10 Stanley Cups can rest easy in the aftermath of a spectacular hockey journey. If it's this Montreal Canadiens legend you are making that assumption about, however, you would be wrong. This 1973 Conn Smythe award winner might trail only former long-time teammate Henri Richard for most Cups in league history (Richard won 11), but he finds himself thinking about one that got away in 1967. As the Hall of Fame winger recalls, his Habs were two-time reigning champs and didn't take the underdog Toronto Maple Leafs seriously enough in that year's Stanley Cup Finals. Hard to feel too bad for him, though!

Question 34

Name this Stanley Cup champion!

For as revered as the actual Stanley Cup trophy is, the customs and traditions that have developed around it stand as an equally significant part of its lore. Every player on the winning team gets their day with the Cup and gets to take a lap around the ice with it in the immediate aftermath of their triumph. For the victory lap of the ice, NHLers have this Hall of Fame forward to thank. After his Detroit Red Wings had won the 1950 Cup, he decided to give fans a closer view by spontaneously toting it around the ice in what would become an annual tradition.

Question 35

Name this Stanley Cup champion!

A popular current commercial for the Enterprise car rental service follows this Hall of Fame goalie around for a look at his supposed post-playing career. On top of driving his pee-wee hockey team - comprised entirely of goaltenders - to practice in his rental car, he is shown strapping his beloved Stanley Cup into a seatbelt on the passenger's side. That trophy features the four-time Vezina winner's name on it three times thanks to his three championships backstopping the New Jersey Devils. His third Cup run in 2003 featured a record seven shutout victories, including three against the Anaheim Mighty Ducks in the Stanley Cup Finals.

Question 36

Name this Stanley Cup champion!

Some hockey players go through entire careers without enjoying the taste of championship success. For this star center, however, it seemed to come at just about every level. Prior to winning two Stanley Cups as a member of the Los Angeles Kings, he had already established himself as a proven winner with a Memorial Cup, World Junior Championship, Calder Cup and Olympic gold medal to his credit. Although he couldn't bring a title to Philadelphia as captain, he got his hands on Stanley twice in the first three years after a 2011 off-season trade landed him with the LA Kings.

Question 37

Name this Stanley Cup champion!

The Stanley Cup stood as something of a bookend on the 15-year career of center Brad Richards. As a 23-year-old in just his fourth NHL season, he first got his hands on Stanley following a Conn Smythe-winning playoff campaign for the Tampa Bay Lightning in which he set an NHL record with seven game-winning goals. More than a decade later, he was a veteran contributor to the Chicago Blackhawks as they won what was their third Cup in six years. This time around, however, the 2004 Lady Byng trophy winner was more of a depth piece on a Blackhawks team that had Jonathan Toews and Patrick Kane leading the way.

Question 38

Name this Stanley Cup champion!

There is no doubting the merits of Sidney Crosby, but “Sid the Kid” has had plenty of help in delivering three Stanley Cups to Pittsburgh since 2009. For proof, look no further than his long-time No. 2 center. While Crosby earned Conn Smythe honors for his 2016 and 2017 playoff performances in leading the Penguins to back-to-back Cup triumphs, the first title for the superstar tandem came as a result of this former Hart trophy winner. Before Crosby had a Conn Smythe to his name, his then-22-year-old teammate was lighting up the postseason with 14 goals and 36 points in 24 games in 2009.

Question 39

Name this Stanley Cup champion!

Raising the Stanley Cup is as good as it gets in the sport of hockey, but this Slovakian star forward might have relished his 2014 triumph as a member of the Los Angeles Kings just that little bit more. For starters, it came against his former team, the New York Rangers. Additionally, by scoring a playoff-leading 14 goals (three more than he had scored in the regular season that year), the three-time All-Star helped position himself for a windfall seven-year contract that following summer that paid him $34 million. He continues to reap the benefits of that contract, although that remains his only Cup experience after over 1,000 games played.

Question 40

Name this Stanley Cup champion!

It’s fitting that a player who is widely regarded as one of the game’s greatest leaders stands as the only NHLer to ever captain two different teams to Stanley Cup glory. The man known as “Moose” sported the ‘C’ while lea ding the Edmonton Oilers to *an unlikely championship in the aftermath of the Wayne Gretzky era in 1990. Perhaps more impressively, however, he captained the New York Rangers to their first Stanley Cup in 54 years in 1994, guaranteeing a Game 6 victory over the rival New Jersey Devils in the Eastern Conference Finals and scoring the Game 7 Cup winner to cement their triumph.

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