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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Ray Toye# | 3 | 2032-2034 | |
| 2 | Jude Anderson | 2 | 2016-2019 | |
| 2 | Joe Black | 2 | 2022-2024 | |
| 2 | Calvin Connor | 2 | 2025-2027 | |
| 2 | Erik Fletcher# | 2 | 2032-2034 | |
| 2 | Manuel García | 2 | 2017-2020 | |
| 2 | Jorge Hernández | 2 | 2012-2014 | |
| 2 | Joël Mastroianni | 2 | 2012-2014 | |
| 2 | Vincenzo Rizzoli# | 2 | 2026-2028 | |
| 2 | Cliff Smith | 2 | 2012-2016 | |
| 2 | Roger Stewart# | 2 | 2029-2030 | |
| 2 | Artie Sullivan | 2 | 2024-2026 | |
| 2 | Mike True# | 2 | 2032-2034 | |
| 2 | Bob Wood# | 2 | 2030-2031 | |
| 2 | Armando Zavagoza | 2 | 2016-2019 | |
| 16 | Mike Allamon# | 1 | 2031-2031 | |
| 16 | Vasco Amore | 1 | 2012-2014 | |
| 16 | Tommy Bartlett | 1 | 2015-2018 | |
| 16 | Geoff Baxter# | 1 | 2031-2031 | |
| 16 | George Bedford | 1 | 2019-2019 | |
| 16 | Edward Benson | 1 | 2026-2028 | |
| 16 | Eddie Black | 1 | 2017-2020 | |
| 16 | John Bradford | 1 | 2022-2024 | |
| 16 | Tomás Bravo# | 1 | 2019-2021 | |
| 16 | Rubén Cabrera# | 1 | 2022-2024 | |
| 16 | Jeremy Callahan | 1 | 2016-2016 | |
| 16 | Danny Campbell# | 1 | 2032-2034 | |
| 16 | Erwin Clark | 1 | 2028-2030 | |
| 16 | Roy Cohn# | 1 | 2029-2030 | |
| 16 | Jeremy Cole | 1 | 2028-2030 | |
| 16 | Dave Conley | 1 | 2021-2023 | |
| 16 | Eric Edwards | 1 | 2016-2019 | |
| 16 | Scott Ellis | 1 | 2020-2021 | |
| 16 | Chris Elwell# | 1 | 2031-2031 | |
| 16 | Rick Emery | 1 | 2016-2016 | |
| 16 | Daniel Farley# | 1 | 2032-2034 | |
| 16 | Jesús Feliciano | 1 | 2012-2015 | |
| 16 | Ernesto Flores | 1 | 2026-2028 | |
| 16 | Dan Fram# | 1 | 2032-2034 | |
| 16 | Matthew Gilmer# | 1 | 2032-2034 | |
| 16 | Joe Graham | 1 | 2022-2024 | |
| 16 | Jason Henderson | 1 | 2022-2024 | |
| 16 | Jake Hickerson# | 1 | 2033-2034 | |
| 16 | Ryan Jenkins | 1 | 2012-2015 | |
| 16 | Danny Jensen# | 1 | 2032-2034 | |
| 16 | John Ketchum# | 1 | 2030-2030 | |
| 16 | Kevin Landry | 1 | 2012-2015 | |
| 16 | David Lawson | 1 | 2015-2018 | |
| 16 | Richard Lawson# | 1 | 2023-2023 | |
| 16 | António López | 1 | 2020-2021 | |
| 16 | Jorge López | 1 | 2018-2021 | |
| 16 | Ed Lott | 1 | 2012-2015 | |
| 16 | Eduardo Marino# | 1 | 2022-2024 | |
| 16 | Marcos Martínez | 1 | 2012-2015 | |
| 16 | Joey McCalvin# | 1 | 2031-2031 | |
| 16 | Cory McCoy# | 1 | 2023-2025 | |
| 16 | Anthony McIntyre | 1 | 2017-2020 | |
| 16 | Beau Miller# | 1 | 2025-2027 | |
| 16 | Brandon Miller | 1 | 2027-2029 | |
| 16 | Jon Morris | 1 | 2015-2018 | |
| 16 | Jason Nash | 1 | 2028-2030 | |
| 16 | Chuck Noblet | 1 | 2014-2017 | |
| 16 | Bill Piner# | 1 | 2029-2030 | |
| 16 | Bryan Powell | 1 | 2012-2014 | |
| 16 | Roger Rogers# | 1 | 2025-2027 | |
| 16 | Kamal Salman | 1 | 2013-2016 | |
| 16 | Scott Selberg | 1 | 2030-2030 | |
| 16 | Hunter Shaw | 1 | 2017-2020 | |
| 16 | Cristián Silva | 1 | 2022-2024 | |
| 16 | John Slater | 1 | 2014-2017 | |
| 16 | Pancho Soriano | 1 | 2026-2029 | |
| 16 | Les Spate | 1 | 2029-2030 | |
| 16 | John Stroud | 1 | 2017-2020 | |
| 16 | Brian Wallace | 1 | 2014-2016 | |
| 16 | Brian Weaver | 1 | 2026-2028 | |
| 16 | Sam Wentzel# | 1 | 2032-2034 | |
| 16 | Cullen Wetmore# | 1 | 2032-2034 | |
| 16 | Kent Williams# | 1 | 2021-2023 | |
| 16 | Buddy Wills | 1 | 2012-2013 | |
| 16 | Kent Young | 1 | 2024-2026 | |
| 81 | J.R. Adams | 0 | 2012-2013 | |
| 81 | Pat Angelil | 0 | 2028-2030 | |
| 81 | Charles Arnold | 0 | 2031-2031 | |
| 81 | George Bagozzi | 0 | 2029-2030 | |
| 81 | Mark Baker | 0 | 2028-2030 | |
| 81 | Mark Bane | 0 | 2026-2028 | |
| 81 | Christian Barnes# | 0 | 2032-2034 | |
| 81 | Jamie Barry# | 0 | 2032-2034 | |
| 81 | Chris Baxter | 0 | 2012-2015 | |
| 81 | Adam Bedell | 0 | 2030-2030 | |
| 81 | Oliver Berkson# | 0 | 2032-2034 | |
| 81 | Elias Bowen# | 0 | 2022-2024 | |
| 81 | Tom Bowen# | 0 | 2031-2031 | |
| 81 | Chris Bradley | 0 | 2022-2024 | |
| 81 | Carter Breault | 0 | 2028-2030 | |
| 81 | Ben Bryant | 0 | 2016-2016 | |
| 81 | Lance Bundy# | 0 | 2032-2034 | |
| 81 | Bobby Bussey | 0 | 2030-2030 | |
| 81 | Mike Butler# | 0 | 2032-2034 | |
| 81 | José Camacho | 0 | 2022-2024 |
