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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 | Luis Alcoser# | 88 | 2005-2021 | |
| 3 | Ryan Hester | 87 | 2001-2011 | |
| 3 | Gabe Vincent# | 87 | 2012-2021 | |
| 5 | Brian Gann | 85 | 2000-2013 | |
| 6 | Sean Cofield# | 83 | 2011-2021 | |
| 7 | Adam Arnett | 79 | 2000-2009 | |
| 8 | Jose Estrada | 77 | 2000-2010 | |
| 9 | Jonathan McMahon | 73 | 2001-2009 | |
| 9 | Justin Messer | 73 | 2000-2012 | |
| 9 | Cameron Outlaw# | 73 | 2015-2021 | |
| 12 | Justin Steach | 72 | 2004-2014 | |
| 13 | Josh Adams | 70 | 2000-2014 | |
| 13 | Federico Gonzalez | 70 | 2000-2009 | |
| 13 | Brad Goodman | 70 | 2012-2021 | |
| 13 | Enrique Perez# | 70 | 2009-2017 | |
| 17 | Dan Hagen | 69 | 2002-2013 | |
| 18 | Jeremy Excell | 68 | 2000-2012 | |
| 18 | Edgar Gonzalez | 68 | 2000-2009 | |
| 18 | Jonathan Lung | 68 | 2000-2011 | |
| 18 | Jonathan Parker# | 68 | 2011-2020 | |
| 18 | Ian Starcher | 68 | 2000-2012 | |
| 23 | Jim Patrick | 67 | 2000-2011 | |
| 24 | Andy Jackson | 65 | 2005-2013 | |
| 24 | Fred Muse | 65 | 2000-2012 | |
| 26 | Nelson Martinez# | 64 | 2011-2021 | |
| 26 | Don Sheffield | 64 | 2000-2011 | |
| 28 | Aaron Harrison | 62 | 2000-2010 | |
| 29 | Cameron Brown | 61 | 2011-2018 | |
| 29 | Dan Cormie | 61 | 2008-2017 | |
| 29 | Santiago Rodas | 61 | 2000-2010 | |
| 29 | Brian Yates | 61 | 2003-2012 | |
| 33 | Andy McCullough | 60 | 2000-2014 | |
| 33 | Ramon Sandoval | 60 | 2000-2009 | |
| 33 | Alan Sweet | 60 | 2000-2009 | |
| 36 | Chris Auger | 59 | 2000-2009 | |
| 36 | Mike Felder | 59 | 2004-2014 | |
| 36 | Markus Mensink | 59 | 2000-2008 | |
| 39 | Matt Garcia | 58 | 2004-2013 | |
| 40 | Tadanori Kawasaki | 57 | 2005-2014 | |
| 40 | Will Moore | 57 | 2000-2009 | |
| 40 | Tom Schauman | 57 | 2003-2010 | |
| 43 | Miguel Gutierres | 56 | 2013-2020 | |
| 43 | Jay Russell | 56 | 2000-2009 | |
| 45 | Logan Johns | 55 | 2002-2011 | |
| 45 | Alex Padial | 55 | 2005-2018 | |
| 47 | Jon Caruso | 54 | 2004-2013 | |
| 47 | Jose Flores | 54 | 2001-2012 | |
| 47 | Jorge Lopez | 54 | 2000-2013 | |
| 47 | Matt Taub | 54 | 2005-2016 | |
| 51 | Nick Giese | 53 | 2000-2009 | |
| 51 | Mike Henken | 53 | 2001-2011 | |
| 51 | Luis Maldonado# | 53 | 2017-2021 | |
| 51 | Sean Prevost | 53 | 2005-2014 | |
| 51 | Jesus Quintero | 53 | 2000-2009 | |
| 51 | Andrew Severson | 53 | 2016-2021 | |
| 57 | Michael Flood | 52 | 2009-2013 | |
| 57 | Gerardo Lozano | 52 | 2014-2021 | |
| 57 | Carlos Martinez | 52 | 2005-2016 | |
| 57 | Paul Reining# | 52 | 2013-2021 | |
| 61 | Daniel Bromley | 51 | 2000-2009 | |
| 61 | Javier Martinez | 51 | 2003-2011 | |
| 61 | Roberto Urias | 51 | 2000-2009 | |
| 64 | Brad Parish | 50 | 2000-2008 | |
| 64 | Chris Pickens | 50 | 2005-2013 | |
| 66 | Rogelio Delgado | 49 | 2005-2012 | |
| 66 | Danny Lopez | 49 | 2000-2011 | |
| 66 | Tony Marcano | 49 | 2000-2014 | |
| 66 | Victor Ortega | 49 | 2000-2008 | |
| 66 | Max Shepherd | 49 | 2012-2016 | |
| 66 | Doug Yost# | 49 | 2007-2021 | |
| 72 | Sam Godsey# | 48 | 2016-2021 | |
| 72 | Ian Harned | 48 | 2000-2010 | |
| 72 | Arturo Jimenez | 48 | 2003-2013 | |
| 72 | Kevin Overholser | 48 | 2000-2010 | |
| 72 | Alex Pina | 48 | 2000-2009 | |
| 77 | Brian Ballengee | 47 | 2016-2021 | |
| 77 | Chad Barber | 47 | 2004-2015 | |
| 77 | Josh Bass# | 47 | 2014-2021 | |
| 77 | Tyler Byrd | 47 | 2000-2011 | |
| 77 | Paul Guidry | 47 | 2000-2008 | |
| 77 | George Kent | 47 | 2014-2021 | |
| 77 | Nick Kline# | 47 | 2007-2018 | |
| 77 | Matt McPeak | 47 | 2000-2006 | |
| 77 | Dustin Robinson | 47 | 2015-2020 | |
| 77 | Morgan Thompson | 47 | 2005-2014 | |
| 77 | Greg Vanrenen | 47 | 2000-2011 | |
| 88 | Mike Banks# | 46 | 2014-2021 | |
| 88 | Robert Bell | 46 | 2005-2016 | |
| 88 | Ken Bixby# | 46 | 2017-2021 | |
| 88 | Seth Bruno | 46 | 2004-2013 | |
| 88 | Miguel Calamaco | 46 | 2010-2015 | |
| 88 | Steve Eck | 46 | 2005-2013 | |
| 88 | Mike Johnson | 46 | 2010-2015 | |
| 88 | Bill Kilmer | 46 | 2000-2006 | |
| 88 | Dan King | 46 | 2009-2015 | |
| 88 | Greg Schultz | 46 | 2010-2018 | |
| 98 | Justin Brooks | 45 | 2012-2020 | |
| 98 | Alfonso Colon | 45 | 2000-2009 | |
| 98 | Ricardo Cortez | 45 | 2005-2012 |
