| Annual | Winner | Loser | Previous BB Websites |
| 09/10 | Andy | Gemma | |
| 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 | |||