| Date | Opponent | Time | Rink | Result | Record |
|---|---|---|---|---|---|
| 11-22-05 | vs. Toms River East (Scrimmage) | 3:45 PM | Winding River | W 6-0 | 0-0 |
| 11-25-05 | @ St. John Vianney (Scrimmage) | 6:30 PM | Wall Ice Rink | L 2-7 | 0-0 |
| 11-30-05 | @ Point Pleasant Borough (Scrimmage) | 4:20 PM | Ocean Ice Palace | W 9-0 | 0-0 |
| 12-02-05 | @ St. Augustine Prep | 5:00 PM | Vineland Ice Arena | L 4-6 | 0-1 |
| 12-05-05 | vs. Red Bank Catholic | 7:30 PM | Winding River | W 5-4 | 1-1 |
| 12-07-05 | @ The Hun School | 5:00 PM | Ice-Land | W 7-5 | 2-1 |
| 12-15-05 | vs. Bishop Eustace Prep | 4:00 PM | Winding River | W 4-3 | 3-1 |
| 12-20-05 | vs. Middletown North | 4:00 PM | Winding River | W 7-1 | 4-1 |
| 12-23-05 | @ Brick | 7:00 PM | Ocean Ice Palace | W 4-2 | 5-1 |
| 12-27-05 | @ Toms River East | 6:00 PM | Winding River | W 3-0 | 6-1 |
| Mayor's Cup Semi-Finals | |||||
| 12-28-05 | vs. Monsignor Donovan | 8:30 PM | Winding River | W 6-1 | 7-1 |
| Mayor's Cup Championship | |||||
| 1-05-06 | vs. St. Augustine Prep | 4:00 PM | Winding River | L 4-7 | 7-2 |
| 1-06-06 | @ Red Bank Catholic | 5:45 PM | Red Bank Armory | L 4-7 | 7-3 |
| 1-10-06 | vs. Middletown South | 4:00 PM | Winding River | W 5-1 | 8-3 |
| 1-12-06 | @ Monsignor Donovan | 4:00 PM | Winding River | L 6-7 | 8-4 |
| 1-16-06 | vs. Monsignor Donovan | 5:00 PM | Winding River | W 5-3 | 9-4 |
| 1-20-06 | @ South Brunswick | 3:45 PM | Princeton Sports Center | W 10-0 | 10-4 |
| 1-23-06 | vs. Old Bridge | 7:30 PM | Winding River | L 5-7 | 10-5 |
| 1-25-06 | @ Bridgewater-Raritan | 4:00 PM | Rock Ice Pavilion | W 3-2 | 11-5 |
| 1-27-06 | @ Bishop Eustace Prep | 5:00 PM | Flyers Skate Zone | L 1-2 | 11-6 |
| 2-02-06 | @ Middletown North | 8:15 PM | Wall Ice Arena | T 4-4 | 11-6-1 |
| 2-07-06 | vs. Brick | 4:00 PM | Winding River | W 6-0 | 12-6-1 |
| 2-09-06 | @ Middletown South | 6:00 PM | Wall Ice Arena | W 5-3 | 13-6-1 |
| 2-13-06 | @ Rumson Fair-Haven | 8:15 PM | Red Bank Armory | W 7-2 | 14-6-1 |
| 2-14-06 | vs. Toms River South | 4:00 PM | Winding River | W 5-1 | 15-6-1 |
| 2-20-06 | vs. Middletown South | 7:30 PM | Winding River | W 6-0 | 16-6-1 |
| Handchen Cup Quarter-Finals | |||||
| 2-22-06 | @ Bishop Eustace | 3:00 PM | Flyers Skate Zone | L 2-3 | 16-7-1 |
| Handchen Cup Semi-Finals | |||||
| 2-28-06 | vs. St. John Vianney | 4:00 PM | Winding River | T 3-3 | 16-7-2 |
| 3-06-06 | vs. Northern Highlands | 7:30 PM | Winding River | W 8-1 | 17-7-2 |
| NJSIAA Public Tournament Round 1 | |||||
| 3-08-06 | vs. Old Bridge | 8:00 PM | Winding River | W 7-3 | 18-7-2 |
| NJSIAA Public Tournament Round 2 | |||||
| 3-13-06 | vs. Bridgewater-Raritan | 6:00 PM | Winding River | W 2-1 | 19-7-2 |
| NJSIAA Public Tournament Quarter-Finals | |||||
| 3-18-06 | @ Randolph | 11:00 AM | Continental Airlines Arena | L 1-3 | 19-8-2 |
| NJSIAA Public Tournament Semi-Finals |