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| Progressive Winning Pct Leaderboard | |
| This table is a snapshot of the career, single-season, active, and yearly leaders at the end of each season. | |
| * - Indicates Hall of Fame
Bold - Indicates active player |
| Year | Career | WPct | Single-Season | WPct | Active | WPct | Yearly | WPct |
| 1952 | Melvin Antonio | .7778 | Melvin Antonio | .7778 | ||||
| 1953 | Harry Robin | .8276 | Harry Robin | .8276 | ||||
| 1954 | Michael Knepper | .6731 | Harry Robin | .8276 | Michael Knepper | .6731 | Dante Ruiz | .7813 |
| 1955 | Dante Ruiz | .6723 | Clyde Pearson | .8333 | Dante Ruiz | .6723 | Clyde Pearson | .8333 |
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