| 100% | UWE | 3 | ___ Krupp who won the Stanley Cup with Colorado Avalanche |
| 60% | ORR | 3 | Bobby ___ who won the Stanley Cup twice with the Boston Bruins |
| 59% | COREYCRAWFORD | 13 | Goalie who won the Stanley Cup three times with 38-Across (2 wds.) |
| 58% | JONATHANTOEWS | 13 | Center and captain who won the Stanley Cup three times with 38-Across (2 wds.) |
| 53% | IGOR | 4 | Larionov who won three Stanley Cups with the Detroit Red Wings as part of their "Russian Five" line |
| 52% | ORR | 3 | NHL player who won the Stanley Cup twice, Bobby |
| 52% | GUY | 3 | Hockey great Lafleur who won five Stanley Cup championships with the Canadiens |
| 44% | ORR | 3 | Bobby ___ who won 2 Stanley Cups for the Boston Bruins |
| 42% | HENRI | 5 | ___ Richard, former NHL player who holds the record for Most Stanley Cup wins with 11 wins |
| 42% | HOCKEY | 6 | Sport played to win the Stanley Cup |
| 41% | NHL | 3 | Group whose champions win the Stanley Cup: Abbr. |
| 41% | NHL | 3 | Group whose champion wins the Stanley Cup: Abbr. |
| 41% | VICTORHEDMAN | 12 | Tampa Bay Lightning defenseman who won the Conn Smythe Trophy for Most Valuable Player during the 2020 Stanley Cup playoffs (2 wds.) |
| 41% | ULF | 3 | Samuelsson who got the winning goal in the 1991 Stanley Cup |
| 41% | ISLANDERS | 9 | Team with four Stanley Cup wins in the 1980s |
| 41% | BLACKHAWKS | 10 | Team with three Stanley Cup wins in the 2010s |
| 41% | CANADIENS | 9 | Team with six Stanley Cup wins in the 1970s |
| 41% | NHL | 3 | Organization whose annual champs win the Stanley Cup: Abbr. |
| 40% | MAPLELEAFS | 10 | Team with five Stanley Cup wins in the 1940s (2 wds.) |
| 40% | HOPE | 4 | Goalie Solo who won two Olympic gold medals and a World Cup championship with the U.S. national soccer team |
| 39% | CANADIENS | 9 | Montreal team with six Stanley Cup wins in the 1970s |
| 39% | BLACKHAWKS | 10 | Chicago team with three Stanley Cup wins in the 2010s |
| 39% | ORR | 3 | Bobby who won two Stanley Cups |
| 39% | ESA | 3 | Tikkanen who won five Stanley Cups |
| 39% | THEBLACKHAWKS | 13 | Chicago NHL team that has won the Stanley Cup six times (2 wds.) |
| 39% | SMALL | 5 | Chris —, snooker player who won the 2002 LG Cup |
| 38% | SANJOSESHARKS | 13 | NHL team based in California that has never won the Stanley Cup: 2 wds. |
| 38% | MAPLELEAFS | 10 | Toronto team with five Stanley Cup wins in the 1940s (2 wds.) |
| 38% | JUSTINROSE | 10 | English golfer who won the 2018 FedEx Cup (2 wds.) |
| 38% | HENRIKSTENSON | 13 | Swedish golfer who won the 2013 FedEx Cup (2 wds.) |