| Year | Name | W | L | Start | End | |
|---|---|---|---|---|---|---|
| 2023 | Kevin Cash | 99 | 63 | Beg | End | |
| 2022 | Kevin Cash | 86 | 76 | Beg | End | |
| 2021 | Kevin Cash | 100 | 62 | Beg | End | |
| 2020 | Kevin Cash | 40 | 20 | Beg | End | |
| 2019 | Kevin Cash | 96 | 66 | Beg | End | |
| 2018 | Kevin Cash | 90 | 72 | Beg | End | |
| 2017 | Kevin Cash | 80 | 82 | Beg | End | |
| 2016 | Kevin Cash | 68 | 94 | Beg | End | |
| 2015 | Kevin Cash | 80 | 82 | Beg | End | |
| 2014 | Joe Maddon | 77 | 85 | Beg | End | |
| 2013 | Joe Maddon | 92 | 71 | Beg | End | |
| 2012 | Joe Maddon | 90 | 72 | Beg | End | |
| 2011 | Joe Maddon | 91 | 71 | Beg | End | |
| 2010 | Joe Maddon | 96 | 66 | Beg | End | |
| 2009 | Joe Maddon | 84 | 78 | Beg | End | |
| 2008 | Joe Maddon | 97 | 65 | Beg | End | |
| 2007 | Joe Maddon | 66 | 96 | Beg | End | |
| 2006 | Joe Maddon | 61 | 101 | Beg | End | |
| 2005 | Lou Piniella | 67 | 95 | Beg | End | |
| 2004 | Lou Piniella | 70 | 91 | Beg | End | |
| 2003 | Lou Piniella | 63 | 99 | Beg | End | |
| 2002 | Hal McRae | 55 | 106 | Beg | End | |
| 2001 | Larry Rothschild | 4 | 10 | Beg | 4/17 | |
| 2001 | Hal McRae | 58 | 90 | 4/18 | End | |
| 2000 | Larry Rothschild | 59 | 79 | Beg | 9/05 | |
| 2000 | Bill Russell | 2 | 1 | 9/06 | 9/08 | |
| 2000 | Larry Rothschild | 8 | 12 | 9/09 | End | |
| 1999 | Larry Rothschild | 69 | 93 | Beg | End | |
| 1998 | Larry Rothschild | 63 | 99 | Beg | End |
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