| 100% | BRASIL | 6 | Five-time winner of the Copa do Mundo |
| 55% | USA | 3 | Five-time winner of the FIBA Basketball World Cup |
| 54% | MINNESOTA | 9 | Five-time winner of the NCAA's Frozen Four championship |
| 54% | USA | 3 | Five-time winner of the FIBA Basketball World Cup (Abbr.) |
| 53% | BRAZIL | 6 | Record five-time winner of the 24-Across |
| 53% | BOSTONCOLLEGE | 13 | Five-time winner of the NCAA's Frozen Four championship (2 wds.) |
| 51% | MESSI | 5 | Five-time winner of FIFA's player of the year award |
| 50% | MESSI | 5 | Winner of the Ballon d'Or seven times |
| 49% | ORR | 3 | Winner of the Norris Trophy for a record eight times |
| 48% | TOM | 3 | With 1-Down, five-time winner of the British Open |
| 46% | MATTBIONDI | 10 | Winner of five swimming gold medals at the 1988 Olympics |
| 46% | BORG | 4 | Winner of Wimbledon five consecutive times between Ashe and McEnroe |
| 46% | WOODS | 5 | Four-time winner of the Masters |
| 45% | PERRYELLIS | 10 | Eight-time winner of the Coty Award |
| 45% | NADAL | 5 | 14-time winner of the French Open |
| 45% | AGASSI | 6 | Four-time winner of the Australian Open |
| 45% | FASTEST | 7 | Done in the least amount of time |
| 45% | PARASITE | 8 | Winner of four 2019 Oscars which did not, apparently, impress the president |
| 45% | BOURQUE | 7 | Ray ___, one of the greatest defensemen in NHL history who is a five-time James Norris Memorial Trophy winner |
| 45% | REDCROSS | 8 | Three-time winner of the Nobel Peace Prize |
| 45% | BAMA | 4 | Nine-time winner of the Sugar Bowl, informally |
| 45% | UTA | 3 | ___ Pippig, three-time winner of the Boston Marathon |
| 45% | THEFRENCHCONNECTION | 19 | Best Picture winner of the 1970s, or what five of this puzzle's answers have |
| 44% | BRAID | 5 | James —, Scottish golfer, five-times winner of The Open Championship, who died in 1950 |
| 44% | KAMALAHARRIS | 12 | Joint winner of Time's Person of the Year for 2020 |
| 44% | RAITT | 5 | 1989 Album of the Year Grammy winner, for “Nick of Time” |
| 44% | KATIE | 5 | Ledecky who has been named World Swimmer of the Year five times |
| 44% | EAGLE | 5 | Creature whose eyesight has four to five times the acuity of humans |
| 43% | ELLEN | 5 | Four-time winner of the Outstanding Talk Show Host Emmy |
| 43% | WISCONSIN | 9 | Six-time winner of the NCAA's Frozen Four championship |