| 100% | JACOBDEGROM | 11 | Mets starting pitcher who won the NL Cy Young Award in 2018 with only 10 wins: 2 wds. |
| 81% | TIMLINCECUM | 11 | Giants starting pitcher who won the NL Cy Young Award in 2009 with only 15 wins: 2 wds. |
| 75% | FELIXHERNANDEZ | 14 | Mariners starting pitcher who won the AL Cy Young Award in 2010 with only 13 wins: 2 wds. |
| 53% | DONNEWCOMBE | 11 | Dodgers pitcher who won both the Cy Young Award and MVP honors in 1956: 2 wds. |
| 53% | CLAYTONKERSHAW | 14 | Dodgers pitcher who won both the Cy Young Award and MVP honors in 2014: 2 wds. |
| 53% | SANDYKOUFAX | 11 | Dodgers pitcher who won both the Cy Young Award and MVP honors in 1963: 2 wds. |
| 52% | JACOBDEGROM | 11 | New York Mets pitcher who won the 2018 National League Cy Young Award (2 wds.) |
| 50% | TREVORBAUER | 11 | Cincinnati Reds starting pitcher who led the National League in ERA and won the 2020 Cy Young Award (2 wds.) |
| 49% | SHANEBIEBER | 11 | Cleveland Indians starting pitcher who won the American League Triple Crown and the 2020 Cy Young Award (2 wds.) |
| 48% | MARTINEZ | 8 | Pitcher Pedro who won the NL Cy Young Award in 1997, and the AL Cy Young Award in 1999 and 2000 |
| 48% | GERRITCOLE | 10 | Right-handed starting pitcher who won the 2023 American League Cy Young Award (2 wds.) |
| 48% | BLAKESNELL | 10 | Left-handed starting pitcher who won the 2023 National League Cy Young Award (2 wds.) |
| 48% | SCHERZER | 8 | Pitcher Max who won the AL Cy Young Award in 2013, and the NL Cy Young Award in 2016 |
| 47% | JOHNSON | 7 | Pitcher Randy who won the AL Cy Young Award in 1995, and the NL Cy Young Award in 1999, 2000, 2001, and 2002 |
| 46% | CLEMENS | 7 | Pitcher Roger who won the AL Cy Young Award in 1986, 1987, 1991, 1997, 1998, and 2001, and the NL Cy Young Award in 2004 |
| 45% | DALLASKEUCHEL | 13 | Astros pitcher who won the 2015 AL Cy Young Award: 2 wds. |
| 45% | MARKDAVIS | 9 | Padres relief pitcher who won the Cy Young in 1989: 2 wds. |
| 45% | ROLLIEFINGERS | 13 | Brewers relief pitcher who won the Cy Young in 1981: 2 wds. |
| 45% | ERICGAGNE | 9 | Dodgers relief pitcher who won the Cy Young in 2003: 2 wds. |
| 45% | JACOB | 5 | Mets pitcher deGrom who won the 2018 and 2019 Cy Young Award |
| 43% | ROGERCLEMENS | 12 | Seven-time Cy Young Award winner who won the award with four different teams: 2 wds. |
| 42% | CORBINBURNES | 12 | Milwaukee Brewers pitcher who won the 2021 National League Cy Young Award (2 wds.) |
| 42% | JAKEPEAVY | 9 | Padres pitcher who won the NL Triple Crown in 2007: 2 wds. |
| 42% | CLAYTONKERSHAW | 14 | Dodgers pitcher who won the NL Triple Crown in 2011: 2 wds. |
| 41% | DAVIDPRICE | 10 | Red Sox pitcher who won two games in the 2018 World Series with a 1.98 ERA (2 wds.) |
| 41% | CHRISSALE | 9 | Braves pitcher who won the NL Triple Crown (wins, ERA, and strikeouts) in 2024: 2 wds. |
| 40% | OREL | 4 | Pitcher Hershiser who won the Cy Young Award in 1988 |
| 40% | MARIANORIVERA | 13 | Yankees relief pitcher who won the MLB Comeback Player of the Year Award in 2013: 2 wds. |
| 40% | SPAHN | 5 | Braves pitcher who won the 1957 Cy Young Award |
| 40% | GREG | 4 | Pitcher Maddux who won the Cy Young Award in four consecutive years |