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| Single-Season Wins Leaderboard | |
| * - Indicates Hall of Fame |
| Rank | Player | Wins | IP | Year | Career Leaderboard |
| 1. | Lewis Washburn | 27 | 257.7 | 2019 | |
| 2. | Korey Mathison | 26 | 261.7 | 2019 | |
| Larry Strope | 26 | 261.0 | 2009 | ||
| 4. | Augustine Stearn | 25 | 242.0 | 2022 | |
| Korey Mathison | 25 | 290.7 | 2021 | ||
| Augustine Stearn | 25 | 248.3 | 2021 | ||
| Freddie Cooley | 25 | 263.3 | 2013 | ||
| Roger Heitman | 25 | 249.0 | 2013 | ||
| 9. | Dennis Baley | 24 | 253.7 | 2022 | |
| David Martinez | 24 | 265.0 | 2019 | ||
| Mark Prior * | 24 | 244.3 | 2011 | ||
| Javier Vazquez | 24 | 280.7 | 2009 | ||
| Jason Schmidt | 24 | 261.3 | 2005 | ||
| 14. | Zachery Hickman | 23 | 245.0 | 2022 | |
| Steven Hildebrant | 23 | 226.0 | 2022 | ||
| Willie Leon | 23 | 250.7 | 2020 | ||
| Silvio Santacruz | 23 | 253.3 | 2017 | ||
| Jose Silas | 23 | 246.3 | 2016 | ||
| Daniel Scott | 23 | 243.0 | 2015 | ||
| Mark Prior * | 23 | 279.3 | 2009 | ||
| Roy Halladay | 23 | 275.0 | 2009 | ||
| Roy Halladay | 23 | 240.7 | 2008 | ||
| 23. | Brian Anderson | 22 | 239.0 | 2022 | |
| Felipe Granados | 22 | 241.3 | 2020 | ||
| Silvio Santacruz | 22 | 232.7 | 2020 | ||
| Freddie Cooley | 22 | 267.7 | 2017 | ||
| Condel Ortiz | 22 | 257.3 | 2017 | ||
| Mark Prior * | 22 | 252.3 | 2013 | ||
| Roy Halladay | 22 | 268.7 | 2010 | ||
| Glen Rakestraw | 22 | 239.7 | 2010 | ||
| Dontrelle Willis | 22 | 220.0 | 2006 | ||
| Mark Buehrle | 22 | 259.0 | 2005 | ||
| Roy Oswalt | 22 | 235.0 | 2005 | ||
| 34. | Lewis Washburn | 21 | 238.0 | 2022 | |
| Brian Anderson | 21 | 252.0 | 2021 | ||
| Brian Anderson | 21 | 263.7 | 2020 | ||
| Felipe Granados | 21 | 263.7 | 2019 | ||
| Silvio Santacruz | 21 | 255.0 | 2019 | ||
| John Moore | 21 | 250.7 | 2019 | ||
| J.D. Martin | 21 | 231.0 | 2018 | ||
| Thomas Gries | 21 | 222.3 | 2018 | ||
| Freddie Cooley | 21 | 257.3 | 2016 | ||
| Jacob Craig | 21 | 229.3 | 2015 | ||
| Joe Morgan Jr. | 21 | 226.0 | 2013 | ||
| Roger Heitman | 21 | 266.3 | 2012 | ||
| Josh Beckett | 21 | 250.3 | 2012 | ||
| Jeremy Bonderman | 21 | 238.7 | 2012 | ||
| Joe Morgan Jr. | 21 | 212.7 | 2012 | ||
| Matt Riley | 21 | 231.0 | 2011 | ||
| Barry Zito | 21 | 293.7 | 2009 | ||
| Glen Rakestraw | 21 | 249.3 | 2009 | ||
| Rick Hummel | 21 | 248.7 | 2009 | ||
| Jeremy Bonderman | 21 | 244.7 | 2008 | ||
| Mark Prior * | 21 | 238.7 | 2008 | ||
| Larry Strope | 21 | 237.3 | 2008 | ||
| Matt Morris | 21 | 235.7 | 2007 | ||
| Jason Schmidt | 21 | 270.3 | 2006 | ||
| Roy Halladay | 21 | 298.3 | 2005 | ||
| Mark Prior * | 21 | 260.7 | 2005 | ||
| Roy Oswalt | 21 | 268.7 | 2004 | ||
| Andy Pettitte | 21 | 239.0 | 2004 | ||
| 62. | Felipe Granados | 20 | 227.7 | 2022 | |
| Lewis Washburn | 20 | 239.0 | 2021 | ||
| Steven Hildebrant | 20 | 225.3 | 2021 | ||
| Adam Muniz | 20 | 224.7 | 2021 | ||
| Joseph Delagarza | 20 | 224.7 | 2021 | ||
| James People | 20 | 213.0 | 2021 | ||
| Henry Mosqueda | 20 | 246.7 | 2020 | ||
| Augustine Stearn | 20 | 243.7 | 2020 | ||
| Amadis Rodriguez | 20 | 237.0 | 2020 | ||
| Brian Anderson | 20 | 285.3 | 2019 | ||
| Amadis Rodriguez | 20 | 252.3 | 2019 | ||
| Nick Younker | 20 | 240.3 | 2019 | ||
| Anthony Lezama | 20 | 236.3 | 2019 | ||
| J.D. Martin | 20 | 234.3 | 2019 | ||
| Roger Heitman | 20 | 224.0 | 2019 | ||
| David Martinez | 20 | 253.3 | 2018 | ||
| Augustine Stearn | 20 | 236.7 | 2018 | ||
| Willian Larson | 20 | 223.0 | 2018 | ||
| Brian Anderson | 20 | 250.7 | 2017 | ||
| Jose Silas | 20 | 250.0 | 2017 | ||
| J.D. Martin | 20 | 224.3 | 2017 | ||
| Roger Heitman | 20 | 245.3 | 2016 | ||
| Condel Ortiz | 20 | 243.0 | 2016 | ||
| Steven Maney | 20 | 215.7 | 2016 | ||
| Carlos Zambrano | 20 | 212.7 | 2016 | ||
| J.D. Martin | 20 | 209.7 | 2016 | ||
| J.D. Martin | 20 | 226.7 | 2015 | ||
| Roger Heitman | 20 | 210.7 | 2015 | ||
| Richard Menzies | 20 | 210.7 | 2015 | ||
| Travis Blackley | 20 | 218.0 | 2014 | ||
| Willian Larson | 20 | 213.3 | 2014 | ||
| Roger Heitman | 20 | 263.0 | 2011 | ||
| Carlos Zambrano | 20 | 230.7 | 2010 | ||
| Josh Beckett | 20 | 222.7 | 2008 | ||
| J.D. Martin | 20 | 218.0 | 2008 | ||
| Roy Halladay | 20 | 266.3 | 2006 | ||
| Barry Zito | 20 | 228.7 | 2006 | ||
| Matt Clement | 20 | 224.0 | 2005 | ||
| 100. | Willie Leon | 19 | 268.7 | 2022 |
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