| 100% | ORR | 3 | Bobby ___ who won 2 Stanley Cups for the Boston Bruins |
| 63% | ORR | 3 | Bobby ___ who won the Stanley Cup twice with the Boston Bruins |
| 51% | ORR | 3 | NHL player who won the Stanley Cup twice, Bobby |
| 49% | ORR | 3 | Bobby who won two Stanley Cups |
| 49% | VICTORHEDMAN | 12 | Tampa Bay Lightning defenseman who won the Conn Smythe Trophy for Most Valuable Player during the 2020 Stanley Cup playoffs (2 wds.) |
| 45% | COREYCRAWFORD | 13 | Goalie who won the Stanley Cup three times with 38-Across (2 wds.) |
| 44% | ORR | 3 | Bobby who once played for the Bruins |
| 44% | JONATHANTOEWS | 13 | Center and captain who won the Stanley Cup three times with 38-Across (2 wds.) |
| 44% | ORR | 3 | Ice hockey legend Bobby ___ who played for the Boston Bruins and Chicago Black Hawks |
| 43% | OREE | 4 | Willie who played for the Boston Bruins |
| 43% | MICHELLEAKERS | 13 | American former soccer player who won the Golden Shoe (now renamed) for scoring 10 goals at the 1991 FIFA Women's World Cup: 2 wds. |
| 42% | UWE | 3 | ___ Krupp who won the Stanley Cup with Colorado Avalanche |
| 41% | LIZAMINNELLI | 12 | "Arthur" actress who won the Best Actress Oscar for "Cabaret": 2 wds. |
| 41% | SALMANRUSHDIE | 13 | Author who won the Booker Prize for "Midnight's Children": 2 wds. |
| 40% | TYRONNLUE | 9 | NBA coach for the Cavaliers who won the championship in 2016: 2 wds. |
| 40% | ELEANORCATTON | 13 | Canadian author who won the Man Booker Prize for "The Luminaries": 2 wds. |
| 40% | IGOR | 4 | Larionov who won three Stanley Cups with the Detroit Red Wings as part of their "Russian Five" line |
| 40% | EDDIESHORE | 10 | Boston Bruin who was the NHL's MVP four times from 1933 to 1938: 2 wds. |
| 40% | KAZUOISHIGURO | 13 | Author who won the Booker Prize for "The Remains of the Day": 2 wds. |
| 40% | ELLENWHITE | 10 | English player who won the Bronze Boot at the 2019 World Cup: 2 wds. |
| 40% | ALEXMORGAN | 10 | US player who won the Silver Boot at the 2019 World Cup: 2 wds. |
| 40% | STEVESMITH | 10 | Panther who won the NFL Receiving Triple Crown for the 2005 season: 2 wds. |
| 40% | STERLINGSHARPE | 14 | Packer who won the NFL Receiving Triple Crown for the 1992 season: 2 wds. |
| 40% | DOMINIKHASEK | 12 | Buffalo Sabre who won the Vezina Trophy for best goaltender six times: 2 wds. |
| 40% | BOBFOSSE | 8 | "All That Jazz" filmmaker who won the Best Director Oscar for "Cabaret": 2 wds. |
| 40% | GEOFFREYRUSH | 12 | Australian actor who won the Best Actor Oscar for 1996's "Shine": 2 wds. |
| 40% | ALEXMORGAN | 10 | U.S. soccer great who won the Silver Boot Award (runner-up for leading goalscorer) at the 2019 FIFA World Cup (2 wds.) |
| 40% | GUY | 3 | Hockey great Lafleur who won five Stanley Cup championships with the Canadiens |
| 39% | NHL | 3 | Organization for the Boston Bruins: Abbr. |
| 39% | CHARLESYU | 9 | Author who won the 2020 National Book Award for Fiction for "Interior Chinatown": 2 wds. |