| Game # | Date | Time | Home | Result | Opponent | Location |
|---|---|---|---|---|---|---|
| 3930482 | 12-05-2019 | 05:00PM | TUCKAHOE HS | L 51 : 55 | WOODLANDS HS | |
| 3874476 | 02-10-2020 | 04:30PM | WOODLANDS HS | W 63 : 46 | BLIND BROOK HS | |
| 3874669 | 02-11-2020 | 04:30PM | PALISADE PREPARATORY HS | L : | WOODLANDS HS | |
| 3874553 | 01-08-2020 | 04:30PM | WOODLANDS HS | W 44 : 20 | LEFFELL SCHOOL | |
| 3874501 | 12-18-2019 | 04:30PM | WOODLANDS HS | W 48 : 35 | TUCKAHOE HS | |
| 3874512 | 01-21-2020 | 04:30PM | YONKERS MONTESSORI ACADEMY | L 27 : 66 | WOODLANDS HS | |
| 3874576 | 01-14-2020 | 04:30PM | WOODLANDS HS | W 34 : 30 | PALISADE PREPARATORY HS | |
| 3874614 | 01-27-2020 | 04:30PM | WOODLANDS HS | W 67 : 30 | YONKERS MONTESSORI ACADEMY | |
| 3874440 | 12-03-2019 | 04:30PM | WOODLANDS HS | W 47 : 32 | WESTLAKE HS | |
| 3874642 | 02-05-2020 | 04:30PM | LEFFELL SCHOOL | L 45 : 55 | WOODLANDS HS | |
| 3980633 | 12-29-2019 | 11:00AM | WOODLANDS HS | L 40 : 50 | NON-REGION OPPONENT | |
| 3874467 | 12-09-2019 | 06:15PM | NORTH SALEM HS | W 54 : 27 | WOODLANDS HS | |
| 3874451 | 02-03-2020 | 04:30PM | BRIARCLIFF HS | W 63 : 38 | WOODLANDS HS | BRIARCLIFF HS |
| 3931941 | 12-07-2019 | 05:00PM | EASTCHESTER HS | W 45 : 24 | WOODLANDS HS | EASTCHESTER HS |
| 3874588 | 01-16-2020 | 04:30PM | WOODLANDS HS | W 1 : 0 | ALEXANDER HAMILTON | FORFEITED CONTEST |
| 3874493 | 01-06-2020 | 04:30PM | ALEXANDER HAMILTON | L 0 : 1 | WOODLANDS HS | FORFEITED CONTEST |
| 3911645 | 02-08-2020 | 01:00PM | WOODLANDS HS | W : | PORT CHESTER HS | HARRISON HS |
| 3895953 | 12-14-2019 | 01:00PM | WOODLANDS HS | L : | NON-REGION OPPONENT | RYE HS |
| 3895952 | 12-13-2019 | 07:00PM | RYE HS | W : | WOODLANDS HS | RYE HS |
| 3911639 | 02-06-2020 | 04:30PM | WOODLANDS HS | L : | HARRISON HS | WOODLANDS HS |
