| Annual | Winner | Loser |
| 06/07 | Kate | Carmine |
| 05/06 | Gino | Ro |
| 04/05 | Nicholas | Rosalyn |
| 03/04 | Joey | Gino |
| 02/03 | Ellen | Mark |
| 01/02 | Joey | Claire |
| 00/01 | Louis | Joey |
| 99/00 | Phil | Joey |
| 98/99 | Bryce | Angie |
| 97/98 | Keith | Louis |
| 96/97 | Nicky | Gino |
| 95/96 | Gino | Phil |
| 94/95 | Angie | Nick Sr. |
| 93/94 | Ellen | Gino |
| 92/93 | Ro | Keith |
| 91/92 | Phil | Nick Sr. |
| 90/91 | Gino | Nick Sr. |
| 89/90 | Andy | Angie |
| 88/89 | Claire | Andy |
| 87/88 | Ro/Bryce | Angie |
| 86/87 | Ellen | Tony |
| 85/86 | Angie | * |
| 84/85 | Nicky | * |
| 83/84 | Keith | * |
| * Stats unavailable | ||
| 87/88-co-winners | ||