| 100% | CARLTON | 7 | Steve, the first pitcher with four Cy Youngs |
| 56% | GREG | 4 | Pitcher Maddux with four Cy Young Awards |
| 49% | GREG | 4 | Maddux with four Cy Youngs |
| 48% | ROGERCLEMENS | 12 | Seven-time Cy Young Award winner who won the award with four different teams: 2 wds. |
| 44% | GREG | 4 | Pitcher Maddux who won the Cy Young Award in four consecutive years |
| 44% | MADDUX | 6 | Greg with four consecutive Cy Youngs |
| 38% | LYLE | 4 | Pitcher Sparky, first American League reliever to win the Cy Young Award |
| 37% | TIMLINCECUM | 11 | Giants starting pitcher who won the NL Cy Young Award in 2009 with only 15 wins: 2 wds. |
| 37% | FELIXHERNANDEZ | 14 | Mariners starting pitcher who won the AL Cy Young Award in 2010 with only 13 wins: 2 wds. |
| 37% | JACOBDEGROM | 11 | Mets starting pitcher who won the NL Cy Young Award in 2018 with only 10 wins: 2 wds. |
| 36% | YUDARVISH | 9 | Five-time All-Star who's the first Japanese pitcher with 2,000 strikeouts in Major League Baseball |
| 36% | BLOB | 4 | Steve McQueen's first major movie, with "The" |
| 36% | SANTA | 5 | With the first parts of 17- and 52-Across and 11- and 25-Down, four California cities |
| 35% | GREG | 4 | Maddux who won four Cy Young Awards |
| 35% | RINGCYCLE | 9 | Musical work in four parts, with its first part opening the Met's 2010-11 season |
| 35% | ALCAPONE | 8 | Noted criminal whose name starts with the same first four letters as where he was imprisoned |
| 35% | PSALM | 5 | The first starts with "Blessed" |
| 35% | OREL | 4 | Pitcher Hershiser who won the Cy Young Award in 1988 |
| 34% | CARLTON | 7 | Only N.L. pitcher to win four Cy Young Awards |
| 34% | GREG | 4 | Pitcher Maddux who won four straight Cy Young Awards |
| 34% | THROWACURVEBALL | 15 | Candy Cummings was the first pitcher to do this |
| 34% | AMAZINGRACE | 11 | The first four-minute mile, e.g.? |
| 34% | SHANE | 5 | 2020 Cy Young pitcher Bieber |
| 33% | DATE | 4 | The first one might end with a kiss |
| 33% | MSDOS | 5 | What the first PCs came with |
| 33% | SPAHN | 5 | Braves pitcher who won the 1957 Cy Young Award |
| 33% | MILKTEETH | 9 | The first set of gnashers of a young mammal |
| 33% | LYLE | 4 | 1977 Cy Young winner from the Yankees |
| 32% | TEN | 3 | Sum of the first four positive integers |
| 32% | SWEEP | 5 | Win the first four World Series games |