| Mon, 8/19/24 to Sun, 8/25/24Week 1 |
| Saturday, August 24, 2024 |
| 9:45 am | Greenwich Country Day | | vs. | Staples Varsity | | Newtown High School |
| 10:30 am | Newtown | | vs. | Staples Varsity | | Newtown High School |
| 12:00 pm | Woodlawn | | vs. | Staples Varsity | | Newtown High School |
| Mon, 8/26/24 to Sun, 9/1/24Week 2 |
| Tuesday, August 27, 2024 |
| 4:00 pm | Bethel | | vs. | Staples Varsity | | Bethel High School - Middle School Turf Soccer Field |
| 4:00 pm | Bethel | | vs. | Staples JV | | Bethel High School - Rockwell Field |
| Thursday, August 29, 2024 |
| 4:00 pm | Hopkins | | vs. | Staples Varsity | | Hopkins |
| 4:00 pm | Hopkins | | vs. | Staples JV | | Hopkins |
| Friday, August 30, 2024 |
| 4:00 pm | Greens Farms Academy | | vs. | Staples Varsity | | Greens Farms Academy - Red Turf Field 2 |
| Mon, 9/2/24 to Sun, 9/8/24Week 3 |
| Tuesday, September 3, 2024 |
| 4:00 pm | Staples Freshman | | vs. | New Canaan | | Staples - Wakeman Field E (grass) |
| 4:30 pm | New Canaan | | vs. | Staples JV | | Saxe Middle School - Field 1 |
| 6:30 pm | New Canaan | | vs. | Staples Varsity | | New Canaan High School - Dunning Stadium |
| Thursday, September 5, 2024 |
| 4:00 pm | Staples Varsity | | vs. | Brien McMahon | | Staples - Wakeman Field B (turf) |
| 4:00 pm | Staples JV | | vs. | Brien McMahon | | Staples - Wakeman Field E (grass) |
| Saturday, September 7, 2024 |
| 6:00 pm | Notre Dame | | vs. | Staples Varsity | | Notre Dame High School - Park Ave Field |
| Sunday, September 8, 2024 |
| —:— — | All Team Event - Visit Hole in the Wall Gang Camp | Hole in the Wall Gang Camp |
| Mon, 9/9/24 to Sun, 9/15/24Week 4 |
| Tuesday, September 10, 2024 |
| 4:00 pm | Staples Varsity | | vs. | Norwalk | | Staples - Wakeman Field B (turf) |
| Wednesday, September 11, 2024 |
| 4:00 pm | Stamford | | vs. | Staples Varsity | | West Beach Field |
| 4:30 pm | Stamford | | vs. | Staples JV | | Stamford High School - Lower multi-sport field |
| Saturday, September 14, 2024 |
| 2:00 pm | Darien | | vs. | Staples Varsity | | Darien High School - Center Oval Turf field |
| 2:00 pm | Darien | | vs. | Staples JV | | Darien High School - Upper Oval Turf field |
| 4:00 pm | Staples Freshman | | vs. | Darien | | Staples - Wakeman Field E (grass) |
| Mon, 9/16/24 to Sun, 9/22/24Week 5 |
| Thursday, September 19, 2024 |
| 4:00 pm | Wilton | | vs. | Staples Freshman | | Allen's Meadow - field 3A |
| 4:00 pm | Staples Varsity | | vs. | Wilton | | Staples - Wakeman Field B (turf) |
| 4:00 pm | Staples JV | | vs. | Wilton | | Staples - Wakeman Field E (grass) |
| Saturday, September 21, 2024 |
| —:— — | GSOCC WSA Day | |
| Mon, 9/23/24 to Sun, 9/29/24Week 6 |
| Tuesday, September 24, 2024 |
| 4:00 pm | Bridgeport Central | | vs. | Staples Varsity | | Bridgeport Central High School - Kennedy Stadium Turf |
| Thursday, September 26, 2024 |
| 4:00 pm | Fairfield Warde | | vs. | Staples JV | | Fairfield Warde High School - Varsity Soccer Grass field |
| 6:00 pm | Fairfield Warde | | vs. | Staples Varsity | | Fairfield Warde High School - Tetreau/Davis field |
| Mon, 9/30/24 to Sun, 10/6/24Week 7 |
| Monday, September 30, 2024 |
| 4:00 pm | Fairfield Ludlowe | | vs. | Staples JV | | Fairfield Ludlowe - Sullivan field |
| 4:00 pm | Staples Freshman | | vs. | Fairfield Ludlowe | | Staples - Wakeman Field E (grass) |
| 7:00 pm | Fairfield Ludlowe | | vs. | Staples Varsity | | Fairfield Ludlowe High School - Taft field |
| Friday, October 4, 2024 |
| 4:00 pm | Staples Varsity | | vs. | Trumbull | | Staples - Wakeman Field B (turf) |
| 4:00 pm | Staples JV | | vs. | Trumbull | | Staples - Wakeman Field E (grass) |
| 4:00 pm | Trumbull | | vs. | Staples Freshman | | Trumbull High School - JV Grass Field |
| Mon, 10/7/24 to Sun, 10/13/24Week 8 |
| Monday, October 7, 2024 |
| —:— — | GSOCC Senior Day | |
| Postponed | Danbury | | vs. | Staples Freshman | | Danbury High School - Grass Soccer field |
| 4:00 pm | Staples Varsity | | vs. | Danbury | | Staples - Wakeman Field B (turf) |
| 4:00 pm | Staples JV | | vs. | Danbury | | Staples - Wakeman Field E (grass) |
| Wednesday, October 9, 2024 |
| 4:00 pm | St. Joseph | | vs. | Staples JV | | St Joseph's High School - Lower Grass field |
| 4:00 pm | St. Joseph | | vs. | Staples Varsity | | St Joseph's High School - Lower Turf |
| Mon, 10/14/24 to Sun, 10/20/24Week 9 |
| Tuesday, October 15, 2024 |
| 4:00 pm | Westhill | | vs. | Staples JV | | Rippowam Middle School - Turf field |
| 4:00 pm | Westhill | | vs. | Staples Varsity | | Westhill High School - Front Turf field |
| 4:30 pm | Staples Freshman | | vs. | Westhill | | Staples - Wakeman Field E (grass) |
| Thursday, October 17, 2024 |
| —:— — | GSOCC Pink Day | |
| 4:00 pm | Ridgefield | | vs. | Staples Freshman | | Ridgefield High School - Upper Grass field |
| 4:00 pm | Staples Varsity | | vs. | Ridgefield | | Staples - Wakeman Field B (turf) |
| 4:00 pm | Staples JV | | vs. | Ridgefield | | Staples - Wakeman Field E (grass) |
| Saturday, October 19, 2024 |
| 11:00 am | Greenwich | | vs. | Staples Freshman | | Greenwich High School - field 3 |
| 11:00 am | Staples Varsity | | vs. | Greenwich | | Staples - Wakeman Field B (turf) |
| 11:00 am | Staples JV | | vs. | Greenwich | | Staples - Wakeman Field E (grass) |
| Sunday, October 20, 2024 |
| —:— — | Push Against Cancer | Jinny Parker Field |
| Mon, 10/21/24 to Sun, 10/27/24Week 10 |
| Tuesday, October 22, 2024 |
| 3:30 pm | Staples Varsity | | vs. | Greenwich | | Staples - Wakeman Field B (turf) |
| Friday, October 25, 2024 |
| 7:00 pm | Staples Varsity | | vs. | New Canaan | | Brien McMahon High School - Pride Field |
| Mon, 10/28/24 to Sun, 11/3/24Week 11 |
| Friday, November 1, 2024 |
| 2:00 pm | Staples Varsity | | vs. | Norwich Academy | | Staples - Wakeman Field B (turf) |
| Mon, 11/4/24 to Sun, 11/10/24Week 12 |
| Monday, November 4, 2024 |
| 2:00 pm | Staples Varsity | | vs. | Newington | | Staples - Wakeman Field B (turf) |
