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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Career Leaderboard |
|---|---|---|---|---|
| 1 | Roger Bailey | .2208 | 2007 | |
| 2 | Derek Duffy | .2407 | 2003 | |
| 3 | Nick Bradley | .2509 | 2006 | |
| 4 | Jair Jurrjens | .2568 | 2013 | |
| 5 | Joel Zumaya | .2601 | 2010 | |
| 6 | Ryan Bowen | .2624 | 1991 | |
| 7 | Marty Harris | .2627 | 2007 | |
| 8 | Joaquin Benoit | .2646 | 2007 | |
| 9 | Malcolm Zegwaard | .2660 | 2012 | |
| 10 | Frank Edwards | .2677 | 2012 | |
| 11 | Paul Phelps | .2687 | 2014 | |
| 12 | Denny Bautista | .2707 | 2007 | |
| 13 | Craig Breslow | .2745 | 2010 | |
| 14 | Dave Márquez | .2762 | 2016 | |
| 15 | Ryan Sherman | .2763 | 2011 | |
| 16 | Craig Breslow | .2779 | 2011 | |
| 17 | António Ortíz | .2795 | 2009 | |
| 18 | Eduardo Ruíz | .2801 | 2024 | |
| 19 | Stephen Strasburg | .2816 | 2011 | |
| 20 | Ken Brandon | .2817 | 2019 | |
| 21 | Elton Anderson | .2836 | 2010 | |
| 22 | Russ Ortiz | .2840 | 1998 | |
| 23 | Kevin Hunnicutt | .2884 | 2009 | |
| 24 | Wynn Cooke | .2886 | 2008 | |
| 25 | Brad Penny | .2889 | 2006 | |
| 26 | Steve Jarvis | .2899 | 2012 | |
| 27 | Melvin Wright | .2902 | 2014 | |
| 28 | Geremi Gonzalez | .2936 | 2007 | |
| 29 | Sweetbreads Mayer | .2954 | 2005 | |
| 30 | Gustavo Chacin | .2957 | 2005 | |
| 31 | Gio Gonzalez | .2963 | 2012 | |
| 32 | Nick Neugebauer | .2966 | 2003 | |
| 33 | Bradley McGuire | .2986 | 2019 | |
| 34 | Chuck Smith | .2990 | 2010 | |
| 35 | Brad Penny | .2996 | 2004 | |
| 36 | Jesse Jones# | .2997 | 2023 | |
| 37 | Kyle Dawson | .2999 | 2012 | |
| 38 | Jason Williams | .3009 | 2015 | |
| 39 | Frank Larkin | .3010 | 2001 | |
| 39 | Mason Mytton | .3010 | 2013 | |
| 41 | Brad Penny | .3011 | 2007 | |
| 42 | Juan Vega | .3013 | 2015 | |
| 43 | Matt Clement | .3017 | 2003 | |
| 44 | Osvaldo Fernandez | .3021 | 1996 | |
| 45 | Ken Smith | .3022 | 2003 | |
| 46 | Steve Hayes | .3024 | 2014 | |
| 47 | Nick Bradley | .3025 | 2007 | |
| 48 | Stephen Smith | .3029 | 2009 | |
| 49 | Chuck Smith | .3051 | 2012 | |
| 50 | Cam Herb | .3052 | 2008 | |
| 51 | Jeff Haley | .3055 | 2008 | |
| 52 | Todd Coffey | .3056 | 2009 | |
| 53 | Ian Kennedy | .3057 | 2009 | |
| 54 | Chris Warren | .3061 | 2016 | |
| 55 | Julio Teheran | .3064 | 2015 | |
| 56 | Ron Wilson | .3067 | 2005 | |
| 57 | Dave Coggin | .3069 | 2002 | |
| 58 | Clarence Burch# | .3074 | 2023 | |
| 59 | Joba Chamberlain | .3077 | 2012 | |
| 59 | Seung-nam Yi | .3077 | 2010 | |
| 61 | Ron Evans | .3080 | 2017 | |
| 62 | Nick Baker | .3081 | 2015 | |
| 63 | Jeff Sawyer | .3086 | 2006 | |
| 64 | Lee Gentry | .3090 | 2001 | |
| 65 | James West | .3092 | 2010 | |
| 66 | Darwin Francis | .3096 | 2010 | |
| 67 | Ned Ames | .3097 | 2015 | |
| 68 | Bob Schultz | .3098 | 2012 | |
| 69 | Joey Hamilton | .3102 | 2007 | |
| 70 | Frank Edwards | .3103 | 2019 | |
| 71 | Fernando Guzmán | .3108 | 2008 | |
| 72 | Brian Wilson | .3110 | 2006 | |
| 72 | Francisco Chimilio | .3110 | 2002 | |
| 74 | Russell Byers# | .3114 | 2021 | |
| 75 | Dave Allen | .3115 | 2008 | |
| 76 | Steve Hayes | .3116 | 2017 | |
| 77 | Woodrow McKee | .3118 | 2017 | |
| 78 | Alejandro Sosa | .3127 | 2007 | |
| 79 | Kyle Grant | .3128 | 2010 | |
| 80 | Denis Boucher | .3129 | 1996 | |
| 81 | Pedro Castro | .3138 | 2012 | |
| 81 | Grant Howard | .3138 | 2021 | |
| 83 | Jason Bere | .3144 | 1994 | |
| 84 | Adam Eaton | .3147 | 2008 | |
| 84 | Stanley High | .3147 | 2017 | |
| 86 | Gio Gonzalez | .3148 | 2013 | |
| 87 | Félix Zamora | .3154 | 2009 | |
| 88 | Chuck Smith | .3156 | 2011 | |
| 89 | Damian Moss | .3158 | 2005 | |
| 90 | Eric Hurley | .3159 | 2005 | |
| 90 | Will Davidson | .3159 | 2013 | |
| 92 | Mike Thurman | .3160 | 2007 | |
| 93 | António Ortíz | .3162 | 2001 | |
| 93 | Júlio Rodríguez | .3162 | 2016 | |
| 95 | Carlos Trinidad | .3163 | 2002 | |
| 96 | Jonathan Jenkins# | .3166 | 2022 | |
| 97 | Nick Bradley | .3169 | 2008 | |
| 98 | Kevin Robinson | .3170 | 2009 | |
| 99 | Takashi Saito | .3173 | 2012 | |
| 100 | Jorge Sosa | .3174 | 2006 |
