| Award | 2005 | 2006 | 2007 | 2008 | 2009 |
| 2yo Male | Syncopation of MSF | Omnipotent of MSF | Roadie of MR | Cat-Az-Trophy of MR | |
| 2yo Filly | Lake Shasta of MR | Dark Water of MR | Blarney Stone of MR | Tuck and Roll of MR | |
| 3yo Male | Last Prayer of MSF | Syncopation of MSF | Red Flag of SLF | Roadie of MR | |
| 3yo Filly | Good Goose of MR | Carnival Note of MR | Dark Water of MR | Blarney Stone of MR | |
| Older Male | Dynaberry of SL | Last Prayer of MSF | Bad Moon Rising of MR | Really Sneaky of MR | |
| Older Female | Maid In Boston of SL | Maid In Boston of SL | Mambo Queen of SLF | Stormy River of MR | |
| Turf Male | Not Awarded | Not Awarded | Bad Moon Rising of MR | Roadie of MR | |
| Turf Female | Not Awarded | Good Goose of MR | Silver Nurse of SL | Get To War of SCS | |
| Sprinter | Not Awarded | Double Strand of MSF | Gone Virginian of MR | Cape Fearless of KR | |
| F/M Sprinter | Not Awarded | Free and Away of MR | Honouramongthieves of SLF | Smarty Q of DR | |
| Miler | Not Awarded | Not Awarded | Not Awarded | Not Awarded | |
| Owner | Not Awarded | Morning Star Farm | Mane'ly Racing | Mane'ly Racing | |
| HOTY | Last Prayer of MSF | Syncopation of MSF | Bad Moon Rising of MR | Roadie of MR |