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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Career Leaderboard |
|---|---|---|---|---|
| 1 | Kirk McCaskill# | .2372 | 1966 | |
| 2 | Bob Sebra# | .2392 | 1968 | |
| 3 | John D'Acquisto# | .2406 | 1966 | |
| 4 | John D'Acquisto# | .2469 | 1968 | |
| 5 | John D'Acquisto# | .2536 | 1965 | |
| 6 | John D'Acquisto# | .2713 | 1969 | |
| 7 | Al McBean# | .2716 | 1968 | |
| 8 | John D'Acquisto# | .2723 | 1964 | |
| 9 | John D'Acquisto# | .2735 | 1963 | |
| 10 | Clay Buchholz# | .2744 | 1964 | |
| 11 | Noah Syndergaard# | .2757 | 1968 | |
| 12 | James Paxton# | .2761 | 1969 | |
| 13 | Jimmie Keenan# | .2762 | 1967 | |
| 14 | Bob Sebra# | .2779 | 1965 | |
| 15 | Don Schwall | .2789 | 1955 | |
| 16 | Hal Gregg# | .2795 | 1967 | |
| 17 | Jimmie Keenan# | .2802 | 1965 | |
| 18 | Jack Hallett | .2804 | 1967 | |
| 19 | Kirk McCaskill# | .2806 | 1968 | |
| 20 | Steve D Barber | .2811 | 1963 | |
| 21 | John Lackey# | .2825 | 1966 | |
| 22 | Paxton Crawford# | .2826 | 1968 | |
| 23 | Jack Hallett | .2837 | 1966 | |
| 24 | Hal Brown# | .2842 | 1967 | |
| 25 | Kerry Wood# | .2845 | 1968 | |
| 26 | Clay Buchholz# | .2855 | 1968 | |
| 27 | Jimmie Keenan# | .2857 | 1964 | |
| 28 | Bob Sebra# | .2864 | 1964 | |
| 29 | Doug Davis# | .2870 | 1967 | |
| 30 | Charlie Root | .2871 | 1953 | |
| 31 | Jaret Wright# | .2889 | 1968 | |
| 32 | Brad Penny# | .2892 | 1968 | |
| 33 | Al McBean# | .2900 | 1966 | |
| 34 | Freddy Garcia# | .2907 | 1968 | |
| 35 | Matt Moore | .2908 | 1953 | |
| 36 | Clay Buchholz# | .2915 | 1960 | |
| 37 | Al Shealy# | .2921 | 1968 | |
| 37 | Jon Lester | .2921 | 1954 | |
| 39 | Randy D Johnson | .2927 | 1947 | |
| 40 | Fritz Peterson# | .2935 | 1968 | |
| 41 | Ownie Carroll | .2938 | 1955 | |
| 42 | Dizzy Dean* | .2980 | 1947 | |
| 43 | James Paxton# | .2984 | 1968 | |
| 44 | Toby Borland | .2990 | 1956 | |
| 45 | Clay Buchholz# | .2991 | 1959 | |
| 46 | Gary Peters | .2995 | 1946 | |
| 47 | Paxton Crawford# | .2997 | 1964 | |
| 48 | Jimmie Keenan# | .3000 | 1968 | |
| 49 | Kirk McCaskill# | .3005 | 1965 | |
| 50 | Hal Gregg# | .3012 | 1969 | |
| 51 | Jim Hickey# | .3019 | 1964 | |
| 52 | Doug Davis# | .3023 | 1968 | |
| 53 | Mat Latos# | .3031 | 1968 | |
| 53 | Mark Mulder | .3031 | 1951 | |
| 55 | Francisco Cordova# | .3032 | 1960 | |
| 56 | Mace Brown# | .3034 | 1968 | |
| 57 | Jack Hallett | .3039 | 1959 | |
| 58 | Kirk McCaskill# | .3040 | 1967 | |
| 59 | Gene Bearden# | .3041 | 1968 | |
| 60 | Atley Donald | .3044 | 1946 | |
| 61 | Snipe Hansen# | .3048 | 1966 | |
| 62 | Steve D Barber | .3049 | 1964 | |
| 63 | Francisco Cordova# | .3055 | 1967 | |
| 63 | Matt Young# | .3055 | 1967 | |
| 65 | Kirk McCaskill# | .3057 | 1961 | |
| 66 | Jaret Wright# | .3060 | 1965 | |
| 67 | Greg Maddux* | .3066 | 1952 | |
| 68 | Shelby Miller | .3069 | 1963 | |
| 69 | John Lackey# | .3076 | 1964 | |
| 70 | Wandy Rodriguez# | .3080 | 1967 | |
| 71 | Mike Bruhert | .3081 | 1954 | |
| 72 | Chuck Taylor# | .3087 | 1967 | |
| 73 | James Paxton# | .3090 | 1964 | |
| 74 | Brad Penny# | .3098 | 1967 | |
| 75 | Mark Mulder | .3100 | 1954 | |
| 76 | Jack Hallett | .3102 | 1958 | |
| 77 | Tim Wakefield# | .3105 | 1968 | |
| 77 | John Lackey# | .3105 | 1961 | |
| 79 | Matt Clement | .3106 | 1952 | |
| 80 | Paxton Crawford# | .3107 | 1967 | |
| 81 | Hal Gregg# | .3109 | 1968 | |
| 81 | Lary Sorensen# | .3109 | 1959 | |
| 81 | James Paxton# | .3109 | 1962 | |
| 81 | Clay Buchholz# | .3109 | 1966 | |
| 85 | Jim Hickey# | .3110 | 1968 | |
| 86 | Jon Lester | .3113 | 1950 | |
| 87 | Steve D Barber | .3115 | 1959 | |
| 87 | Jay Tibbs# | .3115 | 1968 | |
| 89 | Francisco Cordova# | .3117 | 1961 | |
| 90 | Steve D Barber | .3120 | 1961 | |
| 90 | Shelby Miller | .3120 | 1961 | |
| 92 | Jim Maloney | .3123 | 1947 | |
| 93 | Joe Bowman | .3127 | 1946 | |
| 94 | Alex Fernandez | .3133 | 1952 | |
| 95 | Jim Hickey# | .3138 | 1967 | |
| 95 | Shawn Estes# | .3138 | 1959 | |
| 97 | Al Shealy# | .3142 | 1966 | |
| 98 | Stan Coveleski | .3143 | 1952 | |
| 99 | Jack Hallett | .3144 | 1960 | |
| 100 | Hal Gregg# | .3145 | 1966 |
