Perhaps nothing highlights the ignominy of our poor run of results in the first decade of the 21st century like the record breaking run of losses against our former easybeats, St Kilda. From Round 20, 2001, St Kilda would win a record 12 games on the trot against Carlton covering 2002 to 2009 (itself almost a club record for St Kilda against any opponent), before a resurgent Carlton smashed them in 2010:
Now it should be pointed out that St Kilda were a finals team for much of this era, particularly in the large-loss periods of 2003-2005, however, this run of losses remains in stark contract against our Win-Loss record overall against the Saints.
| Fixture | Result | Margin |
| Round 20, 2001 | Won | 44 points |
| Round 1, 2002 | Loss | 24 points |
| Round 16, 2002 | Loss | 43 points |
| Round 7, 2003 | Loss | 12 points |
| Round 20, 2003 | Loss | 91 points |
| Round 10, 2004 | Loss | 108 points |
| Round 15, 2005 | Loss | 80 points |
| Round 8, 2006 | Loss | 92 points |
| Round 6, 2007 | Loss | 43 points |
| Round 17, 2007 | Loss | 10 points |
| Round 2, 2008 | Loss | 40 points |
| Round 15, 2008 | Loss | 32 points |
| Round 12, 2009 | Loss | 9 points |
| Round 7, 2010 | Win | 61 points |
Now it should be pointed out that St Kilda were a finals team for much of this era, particularly in the large-loss periods of 2003-2005, however, this run of losses remains in stark contract against our Win-Loss record overall against the Saints.