| Annual | Winner | Loser | Previous BB Websites |
| "09/10" | Andy | Gemma | Click to see BB 09-10 |
| "08/09" | Bryce Sr | Gary | Click to see BB 08-09 |
| "07/08" | Mike | Gemma | Click to see BB 07-08 |
| "06/07" | Kate | Carmine | Click to see BB 06-07 |
| "05/06" | Gino | Ro | Click to see BB 05-06 |
| "04/05" | Nicholas | Rosalyn | Click to see BB 04-05 |
| "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 | |||