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| Single-Season Caught Stealing Leaderboard | |
| * - Indicates Hall of Fame |
| Rank | Player | Caught Stealing | PA | Year | Career Leaderboard |
| 1. | Harry Bay | 57 | 638 | 1907 | |
| 2. | Harry Bay | 53 | 623 | 1908 | |
| 3. | Elmer Flick * | 45 | 639 | 1911 | |
| 4. | Martin Dihigo | 44 | 620 | 1927 | |
| Frank Chance * | 44 | 632 | 1907 | ||
| 6. | Frank Chance * | 42 | 642 | 1908 | |
| Harry Bay | 42 | 653 | 1906 | ||
| 8. | Curt Walker | 39 | 626 | 1920 | |
| 9. | Clint Thomas | 38 | 615 | 1924 | |
| Elmer Flick * | 38 | 633 | 1909 | ||
| Frank Chance * | 38 | 597 | 1909 | ||
| Topsy Hartsel | 38 | 640 | 1906 | ||
| 13. | Harry Bay | 37 | 593 | 1909 | |
| 14. | Ed Hock | 36 | 662 | 1927 | |
| Fred Clarke | 36 | 646 | 1907 | ||
| Jimmy Slagle | 36 | 620 | 1906 | ||
| 17. | Martin Dihigo | 35 | 575 | 1926 | |
| Frankie Frisch | 35 | 640 | 1924 | ||
| George Carr | 35 | 675 | 1923 | ||
| Homer Smoot * | 35 | 694 | 1912 | ||
| Ward Miller | 35 | 606 | 1912 | ||
| Dave Altizer | 35 | 643 | 1907 | ||
| 23. | Curt Walker | 34 | 639 | 1922 | |
| Joe Jackson | 34 | 662 | 1913 | ||
| Harry Bay | 34 | 551 | 1913 | ||
| Charlie Hemphill | 34 | 661 | 1905 | ||
| Frank Chance * | 34 | 649 | 1904 | ||
| Topsy Hartsel | 34 | 590 | 1902 | ||
| 29. | Chino Smith | 33 | 673 | 1924 | |
| Joe Jackson | 33 | 668 | 1917 | ||
| John Henry Lloyd | 33 | 612 | 1917 | ||
| Joe Connolly | 33 | 598 | 1916 | ||
| Otis Clymer | 33 | 639 | 1906 | ||
| Charlie Hemphill | 33 | 681 | 1904 | ||
| Roy Thomas | 33 | 594 | 1902 | ||
| Frank Chance * | 33 | 566 | 1902 | ||
| Billy Hamilton | 33 | 624 | 1901 | ||
| Elmer Flick * | 33 | 593 | 1901 | ||
| 39. | Frank Warfield | 32 | 618 | 1928 | |
| Bingo Demoss | 32 | 637 | 1918 | ||
| Ginger Beaumont * | 32 | 620 | 1905 | ||
| Elmer Flick * | 32 | 599 | 1902 | ||
| Mike Donlin * | 32 | 633 | 1901 | ||
| 44. | George Carr | 31 | 617 | 1926 | |
| Larry Gardner | 31 | 594 | 1916 | ||
| Ward Miller | 31 | 569 | 1915 | ||
| Ward Miller | 31 | 627 | 1913 | ||
| Del Pratt | 31 | 661 | 1912 | ||
| Al Burch | 31 | 633 | 1912 | ||
| Birdie Cree | 31 | 627 | 1910 | ||
| Harry Bay | 31 | 596 | 1910 | ||
| Frank Chance * | 31 | 582 | 1910 | ||
| Ty Cobb * | 31 | 611 | 1909 | ||
| 54. | Martin Dihigo | 30 | 618 | 1928 | |
| Frank Warfield | 30 | 557 | 1926 | ||
| Martin Dihigo | 30 | 639 | 1925 | ||
| Cool Papa Bell | 30 | 631 | 1925 | ||
| Oscar Charleston | 30 | 613 | 1923 | ||
| Edd Roush | 30 | 619 | 1918 | ||
| Johnny Bates | 30 | 644 | 1917 | ||
| Del Pratt | 30 | 647 | 1914 | ||
| Mickey Doolan | 30 | 587 | 1914 | ||
| Eddie Murphy | 30 | 641 | 1913 | ||
| Del Pratt | 30 | 634 | 1913 | ||
| Sammy Strang | 30 | 608 | 1912 | ||
| Hans Lobert | 30 | 593 | 1911 | ||
| Elmer Flick * | 30 | 625 | 1910 | ||
| Elmer Flick * | 30 | 594 | 1907 | ||
| Roy Thomas | 30 | 646 | 1906 | ||
| Honus Wagner * | 30 | 682 | 1905 | ||
| Frank Chance * | 30 | 644 | 1905 | ||
| Steve Brodie | 30 | 577 | 1901 | ||
| 73. | George Carr | 29 | 570 | 1927 | |
| Chino Smith | 29 | 660 | 1926 | ||
| Bevo Lebourveau | 29 | 607 | 1924 | ||
| Oliver Marcelle | 29 | 571 | 1924 | ||
| Curt Walker | 29 | 581 | 1923 | ||
| Dave Malarcher | 29 | 609 | 1920 | ||
| Oscar Charleston | 29 | 600 | 1919 | ||
| Sam Rice | 29 | 639 | 1916 | ||
| Al Burch | 29 | 632 | 1915 | ||
| Fred Snodgrass | 29 | 584 | 1913 | ||
| Al Bridwell | 29 | 644 | 1912 | ||
| Ward Miller | 29 | 635 | 1911 | ||
| Ty Cobb * | 29 | 619 | 1910 | ||
| Honus Wagner * | 29 | 614 | 1910 | ||
| Emmet Heidrick * | 29 | 599 | 1910 | ||
| Ty Cobb * | 29 | 679 | 1908 | ||
| Wid Conroy | 29 | 690 | 1905 | ||
| Elmer Flick * | 29 | 628 | 1903 | ||
| Frank Chance * | 29 | 557 | 1903 | ||
| 92. | Eddie Dwight | 28 | 548 | 1928 | |
| Ed Hock | 28 | 492 | 1924 | ||
| Jimmy Johnston | 28 | 629 | 1921 | ||
| Dobie Moore | 28 | 563 | 1921 | ||
| George Burns | 28 | 609 | 1919 | ||
| Bevo Lebourveau | 28 | 514 | 1919 | ||
| Johnny Bates | 28 | 599 | 1918 | ||
| George Sisler | 28 | 639 | 1915 | ||
| Ty Cobb * | 28 | 631 | 1915 |
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