| Year | Position | Name |
| 2010 | Winner | Singing Vinnie |
| 1st Runner Up | Repeater & Springer |
|
| 2nd Runner Up | Queen B |
|
| 2009 | Winner | Repeater |
| 1st Runner Up | Springer |
|
| 2nd Runner Up | Queen B |
|
| 3rd Runner Up | Lady Messenger |
|
| 2008 | Winner | Springer |
| 1st Runner Up | Splinter |
|
| 2nd Runner Up | Dynamite |
|
| 3rd Runner Up | Drak |
|
| 2007 | Winner | Dynamite |
| 1st Runner Up | Repeater |
|
| 2nd Runner Up | Gossip |
|
| 2006 | Winner | Queen B |
| 1st Runner Up | Mighty Springer |
|
| 2nd Runner Up | Sunbeam |
|
| 3rd Runner Up | Repeater |
|
| 2005 | Winner | Sun Beam |
| 2004 | Winner | Repeater |
| 2003 | Winner | Mighty Splinter |
| 1st Runner Up | Lady Messenger |
|
| 2nd Runner Up | Lord Anything |
|
| 3rd Runner Up | Repeater |
|
| 2002 | Winner | Lady Messenger |
| 2001 | Winner | Hot Shot |
| 2000 | Winner | Mighty Splinter |
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Festivals Office
Landsome Bowl Cultural Center
The Valley,
Anguilla BWI
tel: (264) 497-8458
sumfest@anguillanet.com