| 100% | MAPLELEAFS | 10 | Toronto team with five Stanley Cup wins in the 1940s (2 wds.) |
| 90% | MAPLELEAFS | 10 | Team with five Stanley Cup wins in the 1940s (2 wds.) |
| 59% | ISLANDERS | 9 | Team with four Stanley Cup wins in the 1980s |
| 59% | BLACKHAWKS | 10 | Team with three Stanley Cup wins in the 2010s |
| 59% | CANADIENS | 9 | Team with six Stanley Cup wins in the 1970s |
| 56% | CANADIENS | 9 | Montreal team with six Stanley Cup wins in the 1970s |
| 56% | BLACKHAWKS | 10 | Chicago team with three Stanley Cup wins in the 2010s |
| 55% | ISLANDERS | 9 | New York team with four Stanley Cup wins in the 1980s |
| 46% | SANJOSESHARKS | 13 | NHL team based in California that has never won the Stanley Cup: 2 wds. |
| 45% | BUFFALOSABRES | 13 | NHL team based in New York that has never won the Stanley Cup: 2 wds. |
| 44% | MINNESOTAWILD | 13 | NHL team based in St. Paul that has never won the Stanley Cup: 2 wds. |
| 43% | ATLANTABRAVES | 13 | Team with which 18-Across won the 1995 World Series: 2 wds. |
| 42% | KELLIEPICKLER | 13 | "American Idol" contestant who teamed with Derek Hough in winning "Dancing with the Stars": 2 wds. |
| 42% | REDWINGS | 8 | Detroit team that did not win the Stanley Cup despite setting the regular season record for most wins in 1996: 2 wds. |
| 42% | BOSTONREDSOX | 12 | Team with which 30-Across won the World Series in 2004: 3 wds. |
| 41% | COREYCRAWFORD | 13 | Goalie who won the Stanley Cup three times with 38-Across (2 wds.) |
| 41% | MATTHEWTKACHUK | 14 | Florida Panthers winger who led the team in scoring in the 2024 Stanley Cup playoffs with 22 points (2 wds.) |
| 40% | OILERS | 6 | N.H.L. team with five championship-winning seasons in the 1980s |
| 40% | THEBLACKHAWKS | 13 | Chicago hockey team with six Stanley Cups (2 wds.) |
| 39% | OILER | 5 | Member of a four-time Stanley Cup-winning team in the 1980s |
| 39% | MILWAUKEEBUCKS | 14 | Team with which 46-Across won a championship in 1971 (2 wds.) |
| 39% | PRIMABALLERINA | 14 | Rank achieved by 16-Across in the 1940s: 2 wds. |
| 39% | ALBERTPUJOLS | 12 | Former Cardinals slugger tied for third place with five grand slam home runs in the 2009 season: 2 wds. |
| 39% | GUY | 3 | Hockey great Lafleur who won five Stanley Cup championships with the Canadiens |
| 38% | JONATHANTOEWS | 13 | Center and captain who won the Stanley Cup three times with 38-Across (2 wds.) |
| 38% | THEBLACKHAWKS | 13 | Chicago NHL team that has won the Stanley Cup six times (2 wds.) |
| 38% | BOSTONBRUINS | 12 | NHL team that lost to 44-Across in the 2019 Stanley Cup Finals (2 wds.) |
| 38% | LIONELRICHIE | 12 | Singer with five #1 songs in the 1980s, including "All Night Long" (2 wds.) |
| 38% | BJORNBORG | 9 | One of only two players in the modern era to win five straight 17-Across Gentlemen's Singles Finals (1976-1980): 2 wds. |
| 38% | ROGERFEDERER | 12 | One of only two players in the modern era to win five straight 17-Across Gentlemen's Singles Finals (2003-2007): 2 wds. |