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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# | 89 | 2015-2024 | |
| 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 | Jose Estrada | 77 | 2000-2010 | |
| 10 | Jonathan McMahon | 73 | 2001-2009 | |
| 10 | Justin Messer | 73 | 2000-2012 | |
| 12 | Justin Steach | 72 | 2004-2014 | |
| 13 | Tom Rise# | 71 | 2015-2024 | |
| 14 | Josh Adams | 70 | 2000-2014 | |
| 14 | Federico Gonzalez | 70 | 2000-2009 | |
| 14 | Brad Goodman | 70 | 2012-2021 | |
| 14 | Enrique Perez | 70 | 2009-2017 | |
| 18 | Dan Hagen | 69 | 2002-2013 | |
| 18 | Nelson Martinez# | 69 | 2011-2023 | |
| 20 | Jeremy Excell | 68 | 2000-2012 | |
| 20 | Edgar Gonzalez | 68 | 2000-2009 | |
| 20 | Jonathan Lung | 68 | 2000-2011 | |
| 20 | Jonathan Parker | 68 | 2011-2022 | |
| 20 | Ian Starcher | 68 | 2000-2012 | |
| 25 | Jim Patrick | 67 | 2000-2011 | |
| 26 | Andy Jackson | 65 | 2005-2013 | |
| 26 | Fred Muse | 65 | 2000-2012 | |
| 28 | Don Sheffield | 64 | 2000-2011 | |
| 29 | Josh Bass# | 63 | 2014-2024 | |
| 30 | Aaron Harrison | 62 | 2000-2010 | |
| 31 | Cameron Brown | 61 | 2011-2018 | |
| 31 | Dan Cormie | 61 | 2008-2017 | |
| 31 | Santiago Rodas | 61 | 2000-2010 | |
| 31 | Brian Yates | 61 | 2003-2012 | |
| 35 | Terry Droubay# | 60 | 2017-2024 | |
| 35 | Andy McCullough | 60 | 2000-2014 | |
| 35 | Ramon Sandoval | 60 | 2000-2009 | |
| 35 | Alan Sweet | 60 | 2000-2009 | |
| 39 | Chris Auger | 59 | 2000-2009 | |
| 39 | Mike Felder | 59 | 2004-2014 | |
| 39 | Luis Maldonado | 59 | 2017-2022 | |
| 39 | Markus Mensink | 59 | 2000-2008 | |
| 43 | Matt Garcia | 58 | 2004-2013 | |
| 44 | Tadanori Kawasaki | 57 | 2005-2014 | |
| 44 | Chris Marquis# | 57 | 2018-2024 | |
| 44 | Will Moore | 57 | 2000-2009 | |
| 44 | Tom Schauman | 57 | 2003-2010 | |
| 48 | Miguel Gutierres | 56 | 2013-2020 | |
| 48 | Nick Kline | 56 | 2007-2023 | |
| 48 | Jay Russell | 56 | 2000-2009 | |
| 51 | Nate Briceno# | 55 | 2014-2024 | |
| 51 | Kyle Connell# | 55 | 2015-2024 | |
| 51 | Alfredo Garza# | 55 | 2012-2024 | |
| 51 | Logan Johns | 55 | 2002-2011 | |
| 51 | Alex Padial | 55 | 2005-2018 | |
| 56 | Jon Caruso | 54 | 2004-2013 | |
| 56 | Jose Flores | 54 | 2001-2012 | |
| 56 | Jorge Lopez | 54 | 2000-2013 | |
| 56 | Donnie Marcus# | 54 | 2016-2023 | |
| 56 | Matt Taub | 54 | 2005-2016 | |
| 61 | Nick Giese | 53 | 2000-2009 | |
| 61 | Mike Henken | 53 | 2001-2011 | |
| 61 | Sean Prevost | 53 | 2005-2014 | |
| 61 | Jesus Quintero | 53 | 2000-2009 | |
| 61 | Andrew Severson | 53 | 2016-2021 | |
| 66 | Colin Esser# | 52 | 2020-2024 | |
| 66 | Michael Flood | 52 | 2009-2013 | |
| 66 | Gerardo Lozano | 52 | 2014-2021 | |
| 66 | Carlos Martinez | 52 | 2005-2016 | |
| 66 | Jeff Mitchell | 52 | 2017-2022 | |
| 66 | Paul Reining# | 52 | 2013-2022 | |
| 72 | Daniel Bromley | 51 | 2000-2009 | |
| 72 | Mickey Ferrell# | 51 | 2010-2023 | |
| 72 | Javier Martinez | 51 | 2003-2011 | |
| 72 | Mauricio Martinez# | 51 | 2015-2024 | |
| 72 | Roberto Urias | 51 | 2000-2009 | |
| 77 | Brad Parish | 50 | 2000-2008 | |
| 77 | Chris Pickens | 50 | 2005-2013 | |
| 79 | Rogelio Delgado | 49 | 2005-2012 | |
| 79 | Cory Gregerson# | 49 | 2014-2024 | |
| 79 | Danny Lopez | 49 | 2000-2011 | |
| 79 | Tony Marcano | 49 | 2000-2014 | |
| 79 | Victor Ortega | 49 | 2000-2008 | |
| 79 | Max Shepherd | 49 | 2012-2016 | |
| 79 | Doug Yost | 49 | 2007-2021 | |
| 86 | Ken Bixby# | 48 | 2017-2023 | |
| 86 | Sam Godsey | 48 | 2016-2022 | |
| 86 | Ian Harned | 48 | 2000-2010 | |
| 86 | Arturo Jimenez | 48 | 2003-2013 | |
| 86 | Kevin Overholser | 48 | 2000-2010 | |
| 86 | Alex Pina | 48 | 2000-2009 | |
| 86 | Rich Roberts# | 48 | 2014-2024 | |
| 93 | Brian Ballengee | 47 | 2016-2021 | |
| 93 | Mike Banks# | 47 | 2014-2023 | |
| 93 | Chad Barber | 47 | 2004-2015 | |
| 93 | Tyler Byrd | 47 | 2000-2011 | |
| 93 | Paul Guidry | 47 | 2000-2008 | |
| 93 | George Kent | 47 | 2014-2021 | |
| 93 | Matt McPeak | 47 | 2000-2006 | |
| 93 | Dustin Robinson | 47 | 2015-2020 |
