| 100% | LONGSHOT | 8 | Team with little chance of winning: 2 wds. |
| 61% | UNDERDOG | 8 | Competitor with little chance of winning |
| 61% | OUTSIDER | 8 | Rank __, someone with little chance of winning |
| 53% | ONIT | 4 | "I wouldn't bet ___!" (very less chance of something happening): 2 wds. |
| 51% | CHICAGOBULLS | 12 | Team with which 32-Across won six NBA titles: 2 wds. |
| 50% | ATLANTABRAVES | 13 | Team with which 18-Across won the 1995 World Series: 2 wds. |
| 47% | LOSTCAUSE | 9 | Person or project with little chance of success |
| 45% | WEIGHTLIFTING | 13 | China holds a record of winning this sport the most number of times with a total of 266 medals: 2 wds. |
| 45% | ICEHOCKEY | 9 | Canada holds a record of winning this sport the most number of times with a total of 21 medals: 2 wds. |
| 45% | MILWAUKEEBUCKS | 14 | Team with which 46-Across won a championship in 1971 (2 wds.) |
| 45% | WEWON | 5 | Cry of the winning team: 2 wds. |
| 44% | MAPLELEAFS | 10 | Team with five Stanley Cup wins in the 1940s (2 wds.) |
| 43% | AFAT | 4 | "I see ___ chance of that happening.": 2 wds. |
| 43% | TREX | 4 | Fearsome dinosaur with little arms: 2 wds. |
| 42% | BSIDE | 5 | Lesser half of a vinyl single: 2 wds. |
| 41% | MAPLELEAFS | 10 | Toronto team with five Stanley Cup wins in the 1940s (2 wds.) |
| 41% | CHICAGOFIRE | 11 | Illinois-based MLS team with a "hot" name: 2 wds. |
| 41% | CALGARYFLAMES | 13 | Alberta-based NHL team with a "hot" name: 2 wds. |
| 41% | PHOENIXSUNS | 11 | Arizona-based NBA team with a "hot" name: 2 wds. |
| 41% | CLOUDY | 6 | "___ With a Chance of Meatballs 2" (2013 animated movie) |
| 41% | MARTINBRODEUR | 13 | Former New Jersey Devils' goaltender who has the highest number of wins with 691 wins and was elected to the Hockey Hall of Fame in 2018: 2 wds. |
| 40% | ORLANDOMAGIC | 12 | Southeastern NBA team with stars in its team logo: 2 wds. |
| 40% | TEXASRANGERS | 12 | Southwestern MLB team with stars in its team logo: 2 wds. |
| 40% | TWELVE | 6 | The chance of rolling it with two dice is 2.78% |
| 40% | UTAHJAZZ | 8 | NBA team with a musical-note logo: 2 wds. |
| 40% | BIGSHOTS | 8 | People with a lot of clout: 2 wds. |
| 40% | BRACKET | 7 | Where teams that have little-to-no chance of winning are found |
| 40% | MINNESOTAWILD | 13 | Midwestern NHL team with a star in its team logo: 2 wds. |
| 39% | KELLIEPICKLER | 13 | "American Idol" contestant who teamed with Derek Hough in winning "Dancing with the Stars": 2 wds. |
| 39% | BOSTONREDSOX | 12 | Team with which 30-Across won the World Series in 2004: 3 wds. |