| 100% | EDMCMAHON | 9 | Johnny Carson sidekick who nearly lost his home to foreclosure in 2008: 2 wds. |
| 32% | BJORNBORG | 9 | Swedish tennis legend nicknamed "Ice Man", who nearly went bankrupt in 1989 following the collapse of his business venture: 2 wds. |
| 30% | KENGRIFFEYJR | 12 | Slugger who hit his 600th home run in 2008: 3 wds. |
| 29% | NICKSIRIANNI | 12 | Eagles head coach who led his team to victory in the 2025 Super Bowl: 2 wds. |
| 29% | SONNYLISTON | 11 | Heavyweight champion who lost that title to 40-Across in 1964: 2 wds. |
| 28% | ALBERTPUJOLS | 12 | Slugger who hit his 600th home run in 2017: 2 wds. |
| 28% | ALEXRODRIGUEZ | 13 | Slugger who hit his 600th home run in 2010: 2 wds. |
| 28% | AMYWINEHOUSE | 12 | "Back to Black" singer who won five Grammy Awards in 2008: 2 wds. |
| 28% | GEORGEFOREMAN | 13 | Heavyweight champion who lost that title to 40-Across in 1974's famous "Rumble in the Jungle": 2 wds. |
| 27% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |
| 26% | JAMESHOLZHAUER | 14 | 2019 "Jeopardy!" contestant who nearly broke the record and is #2 in regular-season winnings ($2,462,216): 2 wds. |
| 26% | JOHNMCCAIN | 10 | Republican senator who ran for president in 2008: 2 wds. |
| 26% | LARRYDAVID | 10 | "Curb Your Enthusiasm" star who gave his Prius to a medical student in 2006: 2 wds. |
| 26% | HASHE | 5 | "___ lost his mind?": 2 wds. |
| 26% | NEWHAVEN | 8 | Home to Yale University: 2 wds. |
| 25% | NOTREDAME | 9 | Home to the Fighting Irish: 2 wds. |
| 25% | DEATHVALLEY | 11 | One of the hottest places on Earth, this place is home to Badwater Basin, point of lowest elevation in North America: 2 wds. |
| 25% | SARAHPALIN | 10 | 18-Across's presidential running mate in 2008: 2 wds. |
| 25% | STEFANEDBERG | 12 | Swedish tennis great who lost to 25-Across in the 1990 Australian Open (2 wds.) |
| 25% | BOSTONCELTICS | 13 | NBA champions who appeared on Wheaties boxes in 2008: 2 wds. |
| 25% | TOONTOWN | 8 | Home to the animations in Who Framed Roger Rabbit |
| 25% | LASVEGAS | 8 | Home to the NHL's Golden Knights: 2 wds. |
| 24% | MIKESCHMIDT | 11 | Phillies slugger who hit the most home runs in the 1980s (313): 2 wds. |
| 24% | JACKPAAR | 8 | Johnny Carson's predecessor at "The Tonight Show": 2 wds. |
| 24% | ALONE | 5 | Home ___ 2: Lost in New York |
| 24% | EDWARDNORTON | 12 | Actor who played the Hulk in 2008's "The Incredible Hulk": 2 wds. |
| 24% | MANUGINOBILI | 12 | Spurs guard who won his fourth NBA championship in 2014: 2 wds. |
| 24% | GREGGPOPOVICH | 13 | Spurs coach who won his fifth NBA championship in 2014: 2 wds. |
| 24% | RUSSELLWILSON | 13 | Seahawks quarterback who gifted his teammates Amazon stock in 2019: 2 wds. |
| 24% | BLEEDINGLOVE | 12 | Leona Lewis song that hit #1 three separate times in 2008: 2 wds. |