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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Juan Gonzalez# | 23 | 2033-2048 | |
| 2 | Kevin Choate* | 15 | 2018-2033 | |
| 3 | Mike Storbeck | 13 | 2031-2047 | |
| 4 | Dan O'Keeffe | 12 | 2030-2045 | |
| 5 | Justin Carrillo | 11 | 2025-2041 | |
| 5 | Seth Chewning | 11 | 2018-2033 | |
| 5 | Karl Gordam# | 11 | 2040-2048 | |
| 5 | Jason Mosier | 11 | 2023-2035 | |
| 5 | Brad Riddick# | 11 | 2033-2048 | |
| 10 | Steven Allen | 10 | 2030-2044 | |
| 10 | Allen George | 10 | 2018-2028 | |
| 10 | Mike Rensi | 10 | 2021-2036 | |
| 13 | Matt Gunnison# | 9 | 2030-2048 | |
| 13 | Josh Pierce# | 9 | 2036-2048 | |
| 13 | Rick Santy | 9 | 2031-2043 | |
| 16 | Neil Bryan | 8 | 2024-2038 | |
| 16 | Kevin Feltes# | 8 | 2037-2048 | |
| 16 | Izzy Marquez | 8 | 2027-2047 | |
| 16 | John Williams | 8 | 2021-2039 | |
| 20 | Efrain Gonzalez | 7 | 2025-2040 | |
| 20 | Mike Pentland | 7 | 2031-2045 | |
| 20 | Mike Rodriguez# | 7 | 2039-2048 | |
| 20 | Jonathan Romero | 7 | 2019-2035 | |
| 20 | Jason Sumrall | 7 | 2023-2042 | |
| 20 | Steve Thomas# | 7 | 2030-2048 | |
| 26 | Tom Call | 6 | 2032-2047 | |
| 26 | Adam Dodson# | 6 | 2035-2047 | |
| 26 | Adrian Ducote# | 6 | 2029-2047 | |
| 26 | Alexis Mendez* | 6 | 2018-2034 | |
| 30 | Donald Burroughs | 5 | 2018-2029 | |
| 30 | Andrew Carroll | 5 | 2025-2042 | |
| 30 | Eric Casale# | 5 | 2031-2047 | |
| 30 | Julian Castro | 5 | 2035-2044 | |
| 30 | Dave Christensen | 5 | 2018-2028 | |
| 30 | Greg Crouse | 5 | 2018-2026 | |
| 30 | Scott Drum* | 5 | 2028-2040 | |
| 30 | Pat Dudding | 5 | 2026-2035 | |
| 30 | Steve Gorter | 5 | 2030-2045 | |
| 30 | Jason Hendsbee# | 5 | 2041-2048 | |
| 30 | John Hoover# | 5 | 2032-2048 | |
| 30 | Jamie Kirchner | 5 | 2027-2046 | |
| 30 | Faddei Madaev | 5 | 2028-2040 | |
| 30 | Jared Marks | 5 | 2018-2028 | |
| 30 | Trenton Peterson# | 5 | 2032-2048 | |
| 30 | Justin Petro | 5 | 2021-2034 | |
| 30 | Matt Robertson | 5 | 2029-2043 | |
| 30 | Alejandro Rodriguez# | 5 | 2041-2048 | |
| 30 | Craig Simon | 5 | 2029-2040 | |
| 30 | Vinny Zavala | 5 | 2033-2045 | |
| 50 | Joey Beaudoin | 4 | 2022-2031 | |
| 50 | Eric Bonner | 4 | 2018-2026 | |
| 50 | Joe Braun# | 4 | 2037-2048 | |
| 50 | Siu-chung Chieu# | 4 | 2034-2048 | |
| 50 | Brian Collins# | 4 | 2035-2048 | |
| 50 | Eddie Constantino | 4 | 2018-2034 | |
| 50 | Daniel Cuevas | 4 | 2018-2028 | |
| 50 | Jon Foster | 4 | 2028-2032 | |
| 50 | Spencer Hay# | 4 | 2042-2048 | |
| 50 | Seung-hyeon Kim | 4 | 2022-2032 | |
| 50 | Alexei Liberman | 4 | 2029-2042 | |
| 50 | Peter Mgulia | 4 | 2032-2044 | |
| 50 | Joe Miller | 4 | 2025-2039 | |
| 50 | Ryan Morales | 4 | 2025-2039 | |
| 50 | Wayne Murphy# | 4 | 2037-2047 | |
| 50 | Randy Nelson# | 4 | 2032-2048 | |
| 50 | Brent Page# | 4 | 2034-2047 | |
| 50 | Josh Reed | 4 | 2031-2044 | |
| 50 | Joey Reeves | 4 | 2018-2023 | |
| 50 | Bill Rich | 4 | 2030-2045 | |
| 50 | Mike Ricketts# | 4 | 2043-2048 | |
| 50 | Alan Scafidi | 4 | 2023-2034 | |
| 50 | Jim Steeb# | 4 | 2034-2048 | |
| 50 | Kwan-wuk Tae# | 4 | 2034-2048 | |
| 50 | Russ Watson | 4 | 2035-2044 | |
| 75 | Steve Anthony | 3 | 2018-2022 | |
| 75 | Brad Brummel | 3 | 2031-2042 | |
| 75 | Ivan Ceballo# | 3 | 2036-2047 | |
| 75 | Gerardo Cruz | 3 | 2018-2025 | |
| 75 | Danny Dudley# | 3 | 2042-2048 | |
| 75 | Rich Edwards | 3 | 2028-2041 | |
| 75 | Noah Ellenbecker# | 3 | 2037-2047 | |
| 75 | Mark Foglesong# | 3 | 2035-2048 | |
| 75 | Danny Garcia | 3 | 2018-2025 | |
| 75 | John Griese# | 3 | 2038-2048 | |
| 75 | Ivan Hassett | 3 | 2033-2044 | |
| 75 | Sergio Hernandez | 3 | 2034-2046 | |
| 75 | Ramon Jacquez# | 3 | 2033-2048 | |
| 75 | Kevin Lowe# | 3 | 2033-2048 | |
| 75 | Justin Madsen# | 3 | 2042-2047 | |
| 75 | J.J. Mason | 3 | 2034-2044 | |
| 75 | Ryan Milana | 3 | 2022-2036 | |
| 75 | Sam Mooney# | 3 | 2040-2048 | |
| 75 | John Nimmo | 3 | 2019-2030 | |
| 75 | Gabe O'Connor | 3 | 2029-2044 | |
| 75 | Rich Palacios | 3 | 2018-2034 | |
| 75 | Andy Pittman# | 3 | 2043-2048 | |
| 75 | Drew Popp | 3 | 2023-2033 | |
| 75 | Tony Ramos# | 3 | 2046-2048 | |
| 75 | Jaiden Randle# | 3 | 2041-2048 | |
| 75 | Evan Roberts# | 3 | 2037-2046 |
