| Mon, 8/25/25 to Sun, 8/31/25Week 1 |
| Monday, August 25, 2025 |
| 10:00 am | Greenwich Academy | | vs. | Staples Varsity | | Greenwich Academy |
| 10:00 am | Staples JV | | vs. | Greenwich Academy | | Staples - Wakeman Field B (turf) |
| Tuesday, August 26, 2025 |
| 4:00 pm | Greens Farms Academy | | vs. | Staples JV | | Greens Farms Academy (Blue Turf Field) |
| 4:00 pm | Greens Farms Academy | | vs. | Staples Varsity | | Greens Farms Academy - Red Turf Field 2 |
| Mon, 9/1/25 to Sun, 9/7/25Week 2 |
| Wednesday, September 3, 2025 |
| 4:00 pm | Staples Varsity | | vs. | New Canaan | | Staples - Wakeman Field B (turf) |
| 4:00 pm | Staples JV | | vs. | New Canaan | | Staples - Wakeman Field E (grass) |
| Friday, September 5, 2025 |
| 4:00 pm | Brien McMahon | | vs. | Staples JV | | Roton Middle School, (Norwalk) |
| 4:15 pm | Brien McMahon | | vs. | Staples Varsity | | Brien McMahon High School - Pride Field |
| Mon, 9/8/25 to Sun, 9/14/25Week 3 |
| Monday, September 8, 2025 |
| 4:30 pm | Norwalk | | vs. | Staples JV | | West Rocks Middle School |
| 6:30 pm | Norwalk | | vs. | Staples Varsity | | West Rocks Middle School |
| Thursday, September 11, 2025 |
| 4:00 pm | Staples Varsity | | vs. | Stamford | | Staples - Wakeman Field B (turf) |
| 4:00 pm | Staples JV | | vs. | Stamford | | Staples - Wakeman Field E (grass) |
| Saturday, September 13, 2025 |
| 6:00 pm | Notre Dame | | vs. | Staples Varsity | | Notre Dame High School - Park Ave Field |
| Mon, 9/15/25 to Sun, 9/21/25Week 4 |
| Monday, September 15, 2025 |
| 4:00 pm | Staples Varsity | | vs. | Darien | | Staples - Wakeman Field B (turf) |
| 4:00 pm | Staples JV | | vs. | Darien | | Staples - Wakeman Field E (grass) |
| Wednesday, September 17, 2025 |
| 5:00 pm | Greenwich | | vs. | Staples Varsity | | Greenwich High Cardinal Stadium |
| 5:00 pm | Greenwich | | vs. | Staples JV | | Greenwich High School - field 3 |
| Friday, September 19, 2025 |
| 4:00 pm | Wilton | | vs. | Staples JV | | Allens Meadow Wilton Field 4 |
| 6:00 pm | Wilton | | vs. | Staples Varsity | | Wilton High (Lilly Field) |
| Mon, 9/22/25 to Sun, 9/28/25Week 5 |
| Thursday, September 25, 2025 |
| 12:00 pm | Staples JV | | vs. | Fairfield Warde | | Staples - Wakeman Field E (grass) |
| 4:00 pm | Staples Varsity | | vs. | Bridgeport Central | | Staples - Wakeman Field B (turf) |
| Saturday, September 27, 2025 |
| 12:00 pm | Staples Varsity | | vs. | Fairfield Warde | | Staples - Wakeman Field B (turf) |
| 4:00 pm | Staples JV | | vs. | Bridgeport Central | | Staples - Wakeman Field E (grass) |
| Mon, 9/29/25 to Sun, 10/5/25Week 6 |
| Tuesday, September 30, 2025 |
| 9:00 am | Trumbull | | vs. | Staples JV | | Trumbull High (Cork Field) |
| 4:00 pm | Staples Varsity | | vs. | Fairfield Ludlowe | | Staples - Wakeman Field B (turf) |
| 4:00 pm | Staples JV | | vs. | Fairfield Ludlowe | | Staples - Wakeman Field E (grass) |
| Saturday, October 4, 2025 |
| 11:00 am | Trumbull | | vs. | Staples Varsity | | Trumbull High (Cork Field) |
| Mon, 10/6/25 to Sun, 10/12/25Week 7 |
| Tuesday, October 7, 2025 |
| 4:00 am | Danbury | | vs. | Staples JV | | Danbury High School - Grass Soccer field |
| 4:00 pm | Danbury | | vs. | Staples Varsity | | Danbury High (Stadium) |
| Friday, October 10, 2025 |
| 4:00 am | Staples JV | | vs. | St. Joseph | | Staples - Wakeman Field E (grass) |
| 4:00 pm | Staples Varsity | | vs. | St. Joseph | | Staples - Wakeman Field B (turf) |
| Mon, 10/13/25 to Sun, 10/19/25Week 8 |
| Tuesday, October 14, 2025 |
| 4:00 am | Staples JV | | vs. | Westhill | | Staples - Wakeman Field E (grass) |
| 4:00 pm | Staples Varsity | | vs. | Westhill | | Staples - Wakeman Field B (turf) |
| Friday, October 17, 2025 |
| 4:00 am | Ridgefield | | vs. | Staples JV | | Ridgefield High School - Upper Grass field |
| 4:00 pm | Ridgefield | | vs. | Staples Varsity | | Ridgefield High (Tiger Hollow Stadium) |
