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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OOPS | YEAR | Open Career Leaderboard |
|---|---|---|---|---|
| 1 | Roger Bailey | .4634 | 2007 | |
| 2 | Derek Duffy | .4814 | 2003 | |
| 3 | Nick Bradley | .4985 | 2006 | |
| 4 | Ken Brandon | .5076 | 2019 | |
| 5 | Jair Jurrjens | .5087 | 2013 | |
| 6 | Dave Márquez | .5270 | 2016 | |
| 7 | Marty Harris | .5271 | 2007 | |
| 8 | Ryan Sherman | .5275 | 2011 | |
| 9 | Denny Bautista | .5285 | 2007 | |
| 10 | Joaquin Benoit | .5344 | 2007 | |
| 11 | Craig Breslow | .5381 | 2010 | |
| 12 | Ian Kennedy | .5413 | 2009 | |
| 13 | Craig Breslow | .5415 | 2011 | |
| 14 | Jonathan Jenkins# | .5416 | 2022 | |
| 15 | Stephen Strasburg | .5424 | 2011 | |
| 16 | Ryan Bowen | .5493 | 1991 | |
| 17 | Russ Ortiz | .5576 | 1998 | |
| 18 | Geremi Gonzalez | .5583 | 2007 | |
| 19 | Joel Zumaya | .5611 | 2010 | |
| 20 | Paul Phelps | .5612 | 2014 | |
| 21 | Jesse Jones# | .5630 | 2023 | |
| 22 | Ryan Harrison | .5635 | 2005 | |
| 23 | Tom Coughlans | .5638 | 2012 | |
| 24 | Stanley High | .5640 | 2017 | |
| 25 | Julio Teheran | .5657 | 2015 | |
| 26 | Juan Vega | .5659 | 2015 | |
| 27 | Elton Anderson | .5662 | 2010 | |
| 28 | Ron Evans | .5669 | 2017 | |
| 28 | Dave Coggin | .5669 | 2002 | |
| 30 | Osvaldo Fernandez | .5674 | 1996 | |
| 31 | Brad Penny | .5685 | 2007 | |
| 32 | Jason Williams | .5689 | 2015 | |
| 33 | Eduardo Ruíz | .5699 | 2024 | |
| 34 | Nick Baker | .5708 | 2015 | |
| 35 | Bradley McGuire | .5727 | 2019 | |
| 36 | Kyle Dawson | .5740 | 2012 | |
| 37 | Les Huggins | .5754 | 2014 | |
| 38 | Tyler Clippard | .5760 | 2009 | |
| 39 | Todd Coffey | .5763 | 2009 | |
| 40 | Bob Schultz | .5770 | 2012 | |
| 41 | Brad Penny | .5782 | 2006 | |
| 42 | Dave Allen | .5783 | 2008 | |
| 43 | Scott Winchester | .5787 | 2003 | |
| 44 | Steve Hayes | .5790 | 2014 | |
| 45 | Jorge Sosa | .5804 | 2006 | |
| 45 | Frank Larkin | .5804 | 2001 | |
| 47 | Steve Hayes | .5807 | 2017 | |
| 48 | Clarence Burch# | .5812 | 2023 | |
| 49 | Bob Foreman | .5824 | 2013 | |
| 50 | Gustavo Chacin | .5834 | 2005 | |
| 51 | Brad Penny | .5835 | 2004 | |
| 52 | Jeff Haley | .5838 | 2008 | |
| 53 | António Ortíz | .5839 | 2009 | |
| 54 | Melvin Wright | .5842 | 2014 | |
| 55 | Wynn Cooke | .5843 | 2008 | |
| 56 | Mike Thurman | .5844 | 2007 | |
| 56 | Kyle Lohse | .5844 | 2012 | |
| 58 | Steve Jarvis | .5847 | 2012 | |
| 59 | Malcolm Zegwaard | .5863 | 2012 | |
| 60 | Chuck Smith | .5864 | 2012 | |
| 61 | Mark Redman | .5868 | 2008 | |
| 62 | Chuck Smith | .5873 | 2010 | |
| 63 | Jesús Pinamango | .5876 | 2008 | |
| 64 | Kris Benson | .5879 | 2007 | |
| 65 | Lee Gentry | .5886 | 2001 | |
| 66 | Jerome Williams | .5887 | 2011 | |
| 67 | Kevin Hunnicutt | .5893 | 2009 | |
| 68 | Floyd Johnston | .5898 | 2008 | |
| 69 | Grant Howard | .5903 | 2021 | |
| 70 | Alejandro Sosa | .5904 | 2007 | |
| 71 | Aaron Goodman | .5909 | 2007 | |
| 72 | Francisco Chimilio | .5915 | 2002 | |
| 73 | Eric Pollock | .5921 | 2005 | |
| 74 | Chris Montgomery | .5923 | 2010 | |
| 75 | Tim Redding | .5925 | 2008 | |
| 76 | Rich Harden | .5933 | 2003 | |
| 77 | Donne Wall | .5935 | 1996 | |
| 78 | Joba Chamberlain | .5938 | 2012 | |
| 79 | Willie E Adams | .5945 | 2008 | |
| 80 | Ned Ames | .5949 | 2015 | |
| 81 | Dan Evans | .5950 | 2013 | |
| 82 | Armando Álvarez | .5962 | 2009 | |
| 83 | Sweetbreads Mayer | .5969 | 2005 | |
| 84 | Will Davidson | .5976 | 2013 | |
| 85 | Mike Maroth | .5979 | 2003 | |
| 86 | Mike Wood | .5982 | 2008 | |
| 87 | Jason Yoder | .5983 | 2023 | |
| 87 | Lee Ollis# | .5983 | 2029 | |
| 87 | Russell Byers# | .5983 | 2021 | |
| 90 | Keith Compton | .5984 | 2010 | |
| 91 | Byron Guffin | .5988 | 2014 | |
| 92 | Mason Mytton | .5997 | 2013 | |
| 93 | Carlos Trinidad | .5998 | 2002 | |
| 94 | António Ortíz | .6000 | 2001 | |
| 94 | Stephen Smith | .6000 | 2009 | |
| 94 | Ryan Jensen | .6000 | 2007 | |
| 97 | Jake Peavy | .6004 | 2002 | |
| 97 | Ameirin Pavlenov | .6004 | 2012 | |
| 99 | Frank Edwards | .6005 | 2012 | |
| 100 | Mike Bishop | .6019 | 2002 |
