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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Matt Beard | 108 | 2000-2013 | |
| 2 | Gabe Vincent | 101 | 2012-2023 | |
| 3 | Cameron Outlaw# | 95 | 2015-2025 | |
| 4 | Luis Alcoser | 88 | 2005-2022 | |
| 5 | Ryan Hester | 87 | 2001-2011 | |
| 6 | Brian Gann | 85 | 2000-2013 | |
| 7 | Sean Cofield | 83 | 2011-2021 | |
| 8 | Adam Arnett | 79 | 2000-2009 | |
| 9 | Josh Bass# | 77 | 2014-2026 | |
| 9 | Jose Estrada | 77 | 2000-2010 | |
| 11 | Terry Droubay# | 76 | 2017-2026 | |
| 12 | Jonathan McMahon | 73 | 2001-2009 | |
| 12 | Justin Messer | 73 | 2000-2012 | |
| 12 | Tom Rise# | 73 | 2015-2026 | |
| 15 | Justin Steach | 72 | 2004-2014 | |
| 16 | Josh Adams | 70 | 2000-2014 | |
| 16 | Federico Gonzalez | 70 | 2000-2009 | |
| 16 | Brad Goodman | 70 | 2012-2021 | |
| 16 | Enrique Perez | 70 | 2009-2017 | |
| 20 | Dan Hagen | 69 | 2002-2013 | |
| 20 | Nelson Martinez# | 69 | 2011-2023 | |
| 22 | Jeremy Excell | 68 | 2000-2012 | |
| 22 | Edgar Gonzalez | 68 | 2000-2009 | |
| 22 | Jonathan Lung | 68 | 2000-2011 | |
| 22 | Jonathan Parker | 68 | 2011-2022 | |
| 22 | Ian Starcher | 68 | 2000-2012 | |
| 27 | Jim Patrick | 67 | 2000-2011 | |
| 28 | Kyle Connell# | 65 | 2015-2026 | |
| 28 | Andy Jackson | 65 | 2005-2013 | |
| 28 | Fred Muse | 65 | 2000-2012 | |
| 28 | Isaiah Robinson# | 65 | 2018-2026 | |
| 32 | Don Sheffield | 64 | 2000-2011 | |
| 33 | Aaron Harrison | 62 | 2000-2010 | |
| 33 | Chris Marquis | 62 | 2018-2025 | |
| 35 | Cameron Brown | 61 | 2011-2018 | |
| 35 | Dan Cormie | 61 | 2008-2017 | |
| 35 | Colin Esser# | 61 | 2020-2026 | |
| 35 | Santiago Rodas | 61 | 2000-2010 | |
| 35 | Brian Yates | 61 | 2003-2012 | |
| 40 | Nate Briceno# | 60 | 2014-2026 | |
| 40 | Andy McCullough | 60 | 2000-2014 | |
| 40 | Ramon Sandoval | 60 | 2000-2009 | |
| 40 | Alan Sweet | 60 | 2000-2009 | |
| 44 | Chris Auger | 59 | 2000-2009 | |
| 44 | Mike Felder | 59 | 2004-2014 | |
| 44 | Luis Maldonado | 59 | 2017-2022 | |
| 44 | Markus Mensink | 59 | 2000-2008 | |
| 44 | Chris Simon# | 59 | 2016-2026 | |
| 49 | Matt Garcia | 58 | 2004-2013 | |
| 50 | Tadanori Kawasaki | 57 | 2005-2014 | |
| 50 | Will Moore | 57 | 2000-2009 | |
| 50 | Tom Schauman | 57 | 2003-2010 | |
| 53 | Alfredo Garza | 56 | 2012-2024 | |
| 53 | Miguel Gutierres | 56 | 2013-2020 | |
| 53 | Nick Kline | 56 | 2007-2023 | |
| 53 | Jay Russell | 56 | 2000-2009 | |
| 53 | D.J. Urbanek# | 56 | 2023-2026 | |
| 58 | Logan Johns | 55 | 2002-2011 | |
| 58 | Alex Padial | 55 | 2005-2018 | |
| 58 | Rich Roberts# | 55 | 2014-2026 | |
| 61 | Jon Caruso | 54 | 2004-2013 | |
| 61 | Jose Flores | 54 | 2001-2012 | |
| 61 | Jorge Lopez | 54 | 2000-2013 | |
| 61 | Donnie Marcus | 54 | 2016-2023 | |
| 61 | Matt Taub | 54 | 2005-2016 | |
| 66 | Justin Baker# | 53 | 2015-2026 | |
| 66 | Nick Giese | 53 | 2000-2009 | |
| 66 | Mike Henken | 53 | 2001-2011 | |
| 66 | Sean Prevost | 53 | 2005-2014 | |
| 66 | Jesus Quintero | 53 | 2000-2009 | |
| 66 | Andrew Severson | 53 | 2016-2021 | |
| 72 | Michael Flood | 52 | 2009-2013 | |
| 72 | Bill Frazer# | 52 | 2022-2026 | |
| 72 | Gerardo Lozano | 52 | 2014-2021 | |
| 72 | Carlos Martinez | 52 | 2005-2016 | |
| 72 | Jeff Mitchell | 52 | 2017-2022 | |
| 72 | Paul Reining | 52 | 2013-2022 | |
| 78 | Daniel Bromley | 51 | 2000-2009 | |
| 78 | Mickey Ferrell | 51 | 2010-2023 | |
| 78 | Rich Mack# | 51 | 2022-2025 | |
| 78 | Javier Martinez | 51 | 2003-2011 | |
| 78 | Mauricio Martinez | 51 | 2015-2024 | |
| 78 | Roberto Urias | 51 | 2000-2009 | |
| 84 | Mike Banks# | 50 | 2014-2026 | |
| 84 | Ryan Barmore# | 50 | 2016-2025 | |
| 84 | Brad Parish | 50 | 2000-2008 | |
| 84 | Chris Pickens | 50 | 2005-2013 | |
| 88 | Rogelio Delgado | 49 | 2005-2012 | |
| 88 | Jesus Fernandez# | 49 | 2014-2025 | |
| 88 | Cory Gregerson# | 49 | 2014-2024 | |
| 88 | Beau Larson# | 49 | 2020-2025 | |
| 88 | Danny Lopez | 49 | 2000-2011 | |
| 88 | Tony Marcano | 49 | 2000-2014 | |
| 88 | Victor Ortega | 49 | 2000-2008 | |
| 88 | Max Shepherd | 49 | 2012-2016 | |
| 88 | Jay Sikora# | 49 | 2013-2025 | |
| 88 | Doug Yost | 49 | 2007-2021 | |
| 98 | Ken Bixby# | 48 | 2017-2023 | |
| 98 | Tony Espinoza# | 48 | 2021-2025 | |
| 98 | Sam Godsey | 48 | 2016-2022 |
