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| Single-Season Caught Stealing Leaderboard | |
| * - Indicates Hall of Fame |
| Rank | Player | Caught Stealing | PA | Year | Career Leaderboard |
| 1. | Luis Rivas | 51 | 639 | 2009 | |
| 2. | Grady Sizemore | 48 | 652 | 2017 | |
| Grady Sizemore | 48 | 683 | 2016 | ||
| 4. | Jason Tyner | 44 | 693 | 2009 | |
| 5. | Juan Pierre | 42 | 562 | 2012 | |
| 6. | Grady Sizemore | 41 | 639 | 2019 | |
| Rickie Weeks | 41 | 674 | 2017 | ||
| 8. | Rickie Weeks | 39 | 658 | 2015 | |
| 9. | Luis Rivas | 38 | 556 | 2010 | |
| 10. | Grady Sizemore | 37 | 537 | 2013 | |
| 11. | Anderson Machado | 36 | 671 | 2009 | |
| 12. | Choo Freeman | 35 | 657 | 2008 | |
| 13. | Grady Sizemore | 34 | 592 | 2018 | |
| Rickie Weeks | 34 | 702 | 2016 | ||
| Grady Sizemore | 34 | 673 | 2011 | ||
| 16. | Tim Moss | 33 | 655 | 2013 | |
| Ardley Jansen | 33 | 621 | 2013 | ||
| Grady Sizemore | 33 | 689 | 2012 | ||
| Rickie Weeks | 33 | 608 | 2009 | ||
| Luis Rivas | 33 | 684 | 2008 | ||
| Ichiro Suzuki | 33 | 614 | 2008 | ||
| 22. | Leopoldo Arguello | 32 | 699 | 2017 | |
| Kyle Walker | 32 | 660 | 2012 | ||
| Anderson Machado | 32 | 625 | 2012 | ||
| Freddie Bynum | 32 | 680 | 2008 | ||
| 26. | Ferdin Tejada | 31 | 669 | 2015 | |
| Corey Patterson | 31 | 627 | 2014 | ||
| Rickie Weeks | 31 | 680 | 2011 | ||
| Ardley Jansen | 31 | 676 | 2011 | ||
| Jason Bay | 31 | 675 | 2010 | ||
| Preston Wilson | 31 | 582 | 2010 | ||
| Shane Victorino | 31 | 588 | 2009 | ||
| Anderson Machado | 31 | 655 | 2008 | ||
| Luis Castillo | 31 | 588 | 2008 | ||
| 35. | Alejandro Machado | 30 | 661 | 2015 | |
| Freddie Bynum | 30 | 702 | 2010 | ||
| Juan Pierre | 30 | 510 | 2009 | ||
| Cesar Crespo | 30 | 459 | 2008 | ||
| 39. | Alejandro Machado | 29 | 674 | 2016 | |
| Grady Sizemore | 29 | 677 | 2015 | ||
| Grady Sizemore | 29 | 658 | 2014 | ||
| Jason Bay | 29 | 657 | 2011 | ||
| Anderson Machado | 29 | 645 | 2011 | ||
| Rickie Weeks | 29 | 640 | 2010 | ||
| Grady Sizemore | 29 | 674 | 2008 | ||
| Preston Wilson | 29 | 654 | 2008 | ||
| Vladimir Guerrero | 29 | 561 | 2008 | ||
| Grady Sizemore | 29 | 673 | 2007 | ||
| Jason Tyner | 29 | 635 | 2007 | ||
| 50. | Daniel Perales | 28 | 690 | 2018 | |
| Trey Webb | 28 | 679 | 2015 | ||
| Tim Moss | 28 | 545 | 2014 | ||
| Ardley Jansen | 28 | 688 | 2012 | ||
| Rickie Weeks | 28 | 661 | 2012 | ||
| Jason Tyner | 28 | 658 | 2011 | ||
| Choo Freeman | 28 | 618 | 2011 | ||
| Rontrez Johnson | 28 | 669 | 2009 | ||
| Anthony Gwynn | 28 | 655 | 2009 | ||
| Jason Tyner | 28 | 638 | 2008 | ||
| Trey Webb | 28 | 629 | 2008 | ||
| 61. | Chris Lubanski | 27 | 659 | 2020 | |
| Felix Veach | 27 | 670 | 2019 | ||
| James Knorr | 27 | 643 | 2018 | ||
| Robert Hernandez | 27 | 533 | 2013 | ||
| Endy Chavez | 27 | 739 | 2010 | ||
| Shin-Soo Choo | 27 | 634 | 2009 | ||
| Mark Kotsay | 27 | 675 | 2008 | ||
| Alejandro Machado | 27 | 655 | 2008 | ||
| 69. | Ryan Seelye | 26 | 697 | 2021 | |
| Gabriel Medina | 26 | 631 | 2021 | ||
| Gabriel Crow | 26 | 618 | 2019 | ||
| Jeremy Reed | 26 | 600 | 2015 | ||
| Bradley Small | 26 | 689 | 2014 | ||
| Choo Freeman | 26 | 626 | 2014 | ||
| Josh Hamilton | 26 | 617 | 2012 | ||
| Shin-Soo Choo | 26 | 707 | 2011 | ||
| Steve Smitherman | 26 | 635 | 2010 | ||
| Mark Kotsay | 26 | 662 | 2009 | ||
| Grady Sizemore | 26 | 562 | 2009 | ||
| Ardley Jansen | 26 | 669 | 2008 | ||
| Josh Hamilton | 26 | 626 | 2008 | ||
| Anderson Machado | 26 | 643 | 2007 | ||
| 83. | Brian Specht | 25 | 672 | 2018 | |
| Chris Snelling | 25 | 663 | 2017 | ||
| Gabriel Crow | 25 | 679 | 2016 | ||
| Juan Vazquez | 25 | 752 | 2015 | ||
| Geronimo Rosales | 25 | 670 | 2014 | ||
| Jackson Melian | 25 | 596 | 2014 | ||
| Corey Hart | 25 | 694 | 2013 | ||
| Manuel Melo | 25 | 673 | 2012 | ||
| Freddie Bynum | 25 | 707 | 2011 | ||
| Grady Sizemore | 25 | 676 | 2010 | ||
| Jason Tyner | 25 | 568 | 2010 | ||
| Dave Krynzel | 25 | 634 | 2007 | ||
| 95. | Johnnie Heuer | 24 | 681 | 2020 | |
| Manuel Arnau | 24 | 707 | 2019 | ||
| Trey Webb | 24 | 678 | 2014 | ||
| Anderson Machado | 24 | 697 | 2013 | ||
| Bradley Small | 24 | 653 | 2013 | ||
| Jackson Melian | 24 | 636 | 2013 |
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