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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Jude Anderson | 2 | 2016-2019 | |
| 1 | Joe Black | 2 | 2022-2024 | |
| 1 | Calvin Connor | 2 | 2025-2027 | |
| 1 | Manuel García | 2 | 2017-2020 | |
| 1 | Jorge Hernández | 2 | 2012-2014 | |
| 1 | Joël Mastroianni | 2 | 2012-2014 | |
| 1 | Vincenzo Rizzoli# | 2 | 2026-2028 | |
| 1 | Cliff Smith | 2 | 2012-2016 | |
| 1 | Roger Stewart# | 2 | 2029-2030 | |
| 1 | Artie Sullivan | 2 | 2024-2026 | |
| 1 | Ray Toye# | 2 | 2032-2033 | |
| 1 | Mike True# | 2 | 2032-2033 | |
| 1 | Bob Wood# | 2 | 2030-2031 | |
| 1 | Armando Zavagoza | 2 | 2016-2019 | |
| 15 | Mike Allamon# | 1 | 2031-2031 | |
| 15 | Vasco Amore | 1 | 2012-2014 | |
| 15 | Tommy Bartlett | 1 | 2015-2018 | |
| 15 | Geoff Baxter# | 1 | 2031-2031 | |
| 15 | George Bedford | 1 | 2019-2019 | |
| 15 | Edward Benson | 1 | 2026-2028 | |
| 15 | Eddie Black | 1 | 2017-2020 | |
| 15 | John Bradford | 1 | 2022-2024 | |
| 15 | Tomás Bravo# | 1 | 2019-2021 | |
| 15 | Rubén Cabrera# | 1 | 2022-2024 | |
| 15 | Jeremy Callahan | 1 | 2016-2016 | |
| 15 | Danny Campbell# | 1 | 2032-2033 | |
| 15 | Erwin Clark | 1 | 2028-2030 | |
| 15 | Roy Cohn# | 1 | 2029-2030 | |
| 15 | Jeremy Cole | 1 | 2028-2030 | |
| 15 | Dave Conley | 1 | 2021-2023 | |
| 15 | Eric Edwards | 1 | 2016-2019 | |
| 15 | Scott Ellis | 1 | 2020-2021 | |
| 15 | Chris Elwell# | 1 | 2031-2031 | |
| 15 | Rick Emery | 1 | 2016-2016 | |
| 15 | Daniel Farley# | 1 | 2032-2033 | |
| 15 | Jesús Feliciano | 1 | 2012-2015 | |
| 15 | Erik Fletcher# | 1 | 2032-2033 | |
| 15 | Ernesto Flores | 1 | 2026-2028 | |
| 15 | Dan Fram# | 1 | 2032-2033 | |
| 15 | Joe Graham | 1 | 2022-2024 | |
| 15 | Jason Henderson | 1 | 2022-2024 | |
| 15 | Ryan Jenkins | 1 | 2012-2015 | |
| 15 | Danny Jensen# | 1 | 2032-2033 | |
| 15 | John Ketchum# | 1 | 2030-2030 | |
| 15 | Kevin Landry | 1 | 2012-2015 | |
| 15 | David Lawson | 1 | 2015-2018 | |
| 15 | Richard Lawson# | 1 | 2023-2023 | |
| 15 | António López | 1 | 2020-2021 | |
| 15 | Jorge López | 1 | 2018-2021 | |
| 15 | Ed Lott | 1 | 2012-2015 | |
| 15 | Eduardo Marino# | 1 | 2022-2024 | |
| 15 | Marcos Martínez | 1 | 2012-2015 | |
| 15 | Bernard Mays# | 1 | 2028-2030 | |
| 15 | Joey McCalvin# | 1 | 2031-2031 | |
| 15 | Cory McCoy# | 1 | 2023-2025 | |
| 15 | Anthony McIntyre# | 1 | 2017-2020 | |
| 15 | Beau Miller# | 1 | 2025-2027 | |
| 15 | Brandon Miller# | 1 | 2027-2029 | |
| 15 | Jon Morris | 1 | 2015-2018 | |
| 15 | Jason Nash | 1 | 2028-2030 | |
| 15 | Chuck Noblet | 1 | 2014-2017 | |
| 15 | Bill Piner# | 1 | 2029-2030 | |
| 15 | Bryan Powell | 1 | 2012-2014 | |
| 15 | Roger Rogers# | 1 | 2025-2027 | |
| 15 | Kamal Salman | 1 | 2013-2016 | |
| 15 | Scott Selberg | 1 | 2030-2030 | |
| 15 | Hunter Shaw | 1 | 2017-2020 | |
| 15 | Cristián Silva | 1 | 2022-2024 | |
| 15 | John Slater | 1 | 2014-2017 | |
| 15 | Pancho Soriano | 1 | 2026-2029 | |
| 15 | Les Spate | 1 | 2029-2030 | |
| 15 | John Stroud# | 1 | 2017-2020 | |
| 15 | Moose Van Sickle# | 1 | 2029-2030 | |
| 15 | Brian Wallace | 1 | 2014-2016 | |
| 15 | Brian Weaver | 1 | 2026-2028 | |
| 15 | Cullen Wetmore# | 1 | 2032-2033 | |
| 15 | Kent Williams# | 1 | 2021-2023 | |
| 15 | Buddy Wills | 1 | 2012-2013 | |
| 15 | Kent Young | 1 | 2024-2026 | |
| 80 | J.R. Adams | 0 | 2012-2013 | |
| 80 | Pat Angelil | 0 | 2028-2030 | |
| 80 | Charles Arnold | 0 | 2031-2031 | |
| 80 | George Bagozzi | 0 | 2029-2030 | |
| 80 | Mark Baker | 0 | 2028-2030 | |
| 80 | Mark Bane | 0 | 2026-2028 | |
| 80 | Christian Barnes# | 0 | 2032-2033 | |
| 80 | Jamie Barry# | 0 | 2032-2033 | |
| 80 | Chris Baxter | 0 | 2012-2015 | |
| 80 | Adam Bedell | 0 | 2030-2030 | |
| 80 | Oliver Berkson# | 0 | 2032-2033 | |
| 80 | Elias Bowen# | 0 | 2022-2024 | |
| 80 | Tom Bowen# | 0 | 2031-2031 | |
| 80 | Chris Bradley | 0 | 2022-2024 | |
| 80 | Carter Breault | 0 | 2028-2030 | |
| 80 | Ben Bryant | 0 | 2016-2016 | |
| 80 | Lance Bundy# | 0 | 2032-2033 | |
| 80 | Bobby Bussey# | 0 | 2030-2030 | |
| 80 | Mike Butler# | 0 | 2032-2033 | |
| 80 | José Camacho | 0 | 2022-2024 | |
| 80 | Robbie Cannon | 0 | 2016-2019 |
