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| Single-Season Wins Leaderboard | |
| * - Indicates Hall of Fame |
| Rank | Player | Wins | IP | Year | Career Leaderboard |
| 1. | Kevin Smith | 30 | 309.0 | 2029 | |
| James Yim * | 30 | 304.0 | 2007 | ||
| 3. | Chad Schmidt | 28 | 259.0 | 2026 | |
| 4. | Roderigo Pequero | 27 | 299.7 | 2024 | |
| David Echegaray | 27 | 280.0 | 2015 | ||
| Ryan Turner * | 27 | 275.7 | 2007 | ||
| Aaron Bacon * | 27 | 336.3 | 2005 | ||
| 8. | Kevin Smith | 26 | 298.0 | 2028 | |
| Danny Day | 26 | 257.3 | 2018 | ||
| Dennis Morelock * | 26 | 289.3 | 2011 | ||
| James Yim * | 26 | 297.7 | 2009 | ||
| 12. | Chad Schmidt | 25 | 292.3 | 2029 | |
| Wayne Sorely | 25 | 247.3 | 2027 | ||
| James Yim * | 25 | 291.7 | 2008 | ||
| Dennis Wright * | 25 | 286.0 | 2008 | ||
| Steven Williams * | 25 | 276.0 | 2008 | ||
| Ryan Turner * | 25 | 296.7 | 2006 | ||
| Jeffrey Cargo | 25 | 257.0 | 2006 | ||
| Samson Steele * | 25 | 315.3 | 2003 | ||
| 20. | Richard San Juan | 24 | 299.7 | 2029 | |
| Xalbador Laguna | 24 | 237.0 | 2027 | ||
| Roderigo Pequero | 24 | 268.7 | 2023 | ||
| Jonathan Alexander | 24 | 249.0 | 2023 | ||
| Ramon Cordova | 24 | 264.0 | 2021 | ||
| Aaron Bacon * | 24 | 269.0 | 2008 | ||
| Mark Torrence | 24 | 322.7 | 2005 | ||
| Dmitrij Mitskevich | 24 | 287.0 | 2005 | ||
| Aaron Bacon * | 24 | 331.0 | 2004 | ||
| Joseph Seybert | 24 | 266.3 | 2003 | ||
| 30. | Armando Mesta | 23 | 256.7 | 2029 | |
| Richard San Juan | 23 | 272.0 | 2028 | ||
| Kevin Smith | 23 | 278.7 | 2027 | ||
| Kevin Smith | 23 | 276.7 | 2026 | ||
| Armando Mesta | 23 | 257.0 | 2025 | ||
| Jacob Perl | 23 | 268.7 | 2023 | ||
| Ralph Ives | 23 | 255.7 | 2023 | ||
| Kazuma Sen | 23 | 234.0 | 2023 | ||
| Randall Spates | 23 | 293.7 | 2010 | ||
| Ryan Turner * | 23 | 271.7 | 2008 | ||
| Andrew Albury | 23 | 230.7 | 2006 | ||
| Leonard Lubbers | 23 | 247.3 | 2003 | ||
| 42. | Richard San Juan | 22 | 262.3 | 2027 | |
| Dennis Couch | 22 | 240.0 | 2027 | ||
| Wilfredo Arroyo | 22 | 234.0 | 2027 | ||
| Wayne Sorely | 22 | 257.3 | 2025 | ||
| Manuel Nieves | 22 | 245.3 | 2024 | ||
| Chale Crespa | 22 | 239.7 | 2024 | ||
| Ralph Ives | 22 | 263.0 | 2021 | ||
| Artur Sax | 22 | 238.7 | 2019 | ||
| David Echegaray | 22 | 227.0 | 2017 | ||
| David Echegaray | 22 | 246.3 | 2016 | ||
| Aaron Bacon * | 22 | 250.0 | 2011 | ||
| James Yim * | 22 | 271.7 | 2010 | ||
| Scott Bartell | 22 | 289.0 | 2009 | ||
| Dennis Morelock * | 22 | 277.7 | 2009 | ||
| Mark Torrence | 22 | 325.7 | 2008 | ||
| Armand Banuelos | 22 | 268.3 | 2008 | ||
| Andrew Albury | 22 | 216.3 | 2008 | ||
| Aaron Bacon * | 22 | 267.3 | 2006 | ||
| Kelvin Palen | 22 | 291.0 | 2005 | ||
| Kelvin Palen | 22 | 285.0 | 2004 | ||
| Edgardo Castillo * | 22 | 281.7 | 2004 | ||
| Andrew Albury | 22 | 249.7 | 2003 | ||
| David Scoggin | 22 | 277.3 | 2002 | ||
| 65. | Ralph Ives | 21 | 265.3 | 2029 | |
| Chad Schmidt | 21 | 280.7 | 2028 | ||
| Wilfredo Arroyo | 21 | 264.7 | 2028 | ||
| Pete Leighburn | 21 | 262.7 | 2027 | ||
| Kevin Smith | 21 | 272.0 | 2025 | ||
| Higinio Delmonte | 21 | 254.0 | 2025 | ||
| Kevin Smith | 21 | 267.0 | 2024 | ||
| Ramon Cordova | 21 | 236.3 | 2022 | ||
| Kevin Smith | 21 | 267.0 | 2021 | ||
| Richard San Juan | 21 | 256.3 | 2021 | ||
| David Echegaray | 21 | 256.3 | 2020 | ||
| Carmine Whittingham | 21 | 220.7 | 2018 | ||
| James Alexander | 21 | 250.3 | 2016 | ||
| Ryan Turner * | 21 | 250.7 | 2014 | ||
| James Yim * | 21 | 251.3 | 2013 | ||
| Art Toczek * | 21 | 245.0 | 2013 | ||
| J.J. Cobb | 21 | 248.0 | 2011 | ||
| George Aybar | 21 | 254.3 | 2010 | ||
| George Stoehr | 21 | 250.0 | 2010 | ||
| Robert Garza * | 21 | 238.7 | 2010 | ||
| Leo Cleland * | 21 | 250.7 | 2009 | ||
| Alex Ramirez | 21 | 230.3 | 2009 | ||
| Clarence McNatt * | 21 | 283.3 | 2008 | ||
| Jeeves Vanhooten | 21 | 289.3 | 2007 | ||
| Dennis Morelock * | 21 | 258.3 | 2007 | ||
| Leonard Lubbers | 21 | 257.3 | 2007 | ||
| Joseph Smartt | 21 | 242.0 | 2007 | ||
| Ryan Turner * | 21 | 283.7 | 2005 | ||
| Malik Meng | 21 | 278.7 | 2005 | ||
| Dan Entrekin | 21 | 267.0 | 2004 | ||
| Armando Quinonez * | 21 | 242.3 | 2004 | ||
| Willie Marshall | 21 | 222.3 | 2004 | ||
| Steven Williams * | 21 | 283.7 | 2003 | ||
| Armando Quinonez * | 21 | 256.7 | 2003 | ||
| Benjamin Alcala | 21 | 261.3 | 2002 | ||
| Armando Quinonez * | 21 | 253.7 | 2002 |
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