| Round 1 |
|---|
| 1 |  | Fairfield Ludlowe High School Falcons | 1-2-4 | vs | 3-5-6 | Marblehead High School Fishwagons |  |
| 2 |  | Greenwich Academy Gators | 2-3-5 | vs | 1-4-6 | Dartmouth High School Sailing |  |
| 3 |  | Darien High School Blue Wave | 2-4-5 | vs | 1-3-6 | East Greenwich High School Avengers |  |
| 4 |  | Greens Farms Academy Dragons | 1-2-3 | vs | 4-5-6 | St. Johns Prep Eagles |  |
| 5 | | Fairfield Ludlowe High School Falcons | 3-5-6 | vs | 1-2-4 | Greenwich Academy Gators | |
| 6 | | East Greenwich High School Avengers | 2-3-5 | vs | 1-4-6 | Marblehead High School Fishwagons | |
| 7 | | St. Johns Prep Eagles | 2-4-5 | vs | 1-3-6 | Dartmouth High School Sailing | |
| 8 | | Greens Farms Academy Dragons | 1-2-6 | vs | 3-4-5 | Darien High School Blue Wave | |
| 9 | | Greenwich Academy Gators | 1-2-6 | vs | 3-4-5 | East Greenwich High School Avengers | |
| 10 | | Fairfield Ludlowe High School Falcons | 1-2-3 | vs | 4-5-6 | St. Johns Prep Eagles | |
| 11 | | Darien High School Blue Wave | 1-3-4 | vs | 2-5-6 | Marblehead High School Fishwagons | |
| 12 | | Greens Farms Academy Dragons | 1-3-5 | vs | 2-4-6 | Dartmouth High School Sailing | |
| 13 | | St. Johns Prep Eagles | 2-4-5 | vs | 1-3-6 | East Greenwich High School Avengers | |
| 14 | | Greenwich Academy Gators | 1-2-5 | vs | 3-4-6 | Darien High School Blue Wave | |
| 15 | | Dartmouth High School Sailing | 1-4-6 | vs | 2-3-5 | Fairfield Ludlowe High School Falcons | |
| 16 | | Greens Farms Academy Dragons | 1-2-6 | vs | 3-4-5 | Marblehead High School Fishwagons | |
| 17 | | Darien High School Blue Wave | 1-2-5 | vs | 3-4-6 | St. Johns Prep Eagles | |
| 18 | | East Greenwich High School Avengers | 3-4-5 | vs | 1-2-6 | Dartmouth High School Sailing | |
| 19 | | Marblehead High School Fishwagons | 3-4-6 | vs | 1-2-5 | Greenwich Academy Gators | |
| 20 | | Fairfield Ludlowe High School Falcons | 2-4-5 | vs | 1-3-6 | Greens Farms Academy Dragons | |
| 21 | | Dartmouth High School Sailing | 3-4-6 | vs | 1-2-5 | Darien High School Blue Wave | |
| 22 | | St. Johns Prep Eagles | 1-2-3 | vs | 4-5-6 | Marblehead High School Fishwagons | |
| 23 | | East Greenwich High School Avengers | 3-4-6 | vs | 1-2-5 | Fairfield Ludlowe High School Falcons | |
| 24 | | Greens Farms Academy Dragons | 3-4-5 | vs | 1-2-6 | Greenwich Academy Gators | |
| 25 | | Marblehead High School Fishwagons | 4-5-6 | vs | 1-2-3 | Dartmouth High School Sailing | |
| 26 | | Fairfield Ludlowe High School Falcons | 3-4-6 | vs | 1-2-5 | Darien High School Blue Wave | |
| 27 | | Greenwich Academy Gators | 1-2-6 | vs | 3-4-5 | St. Johns Prep Eagles | |
| 28 | | Greens Farms Academy Dragons | 1-3-4 | vs | 2-5-6 | East Greenwich High School Avengers | |
| Round 2 |
|---|
| 29 | | Fairfield Ludlowe High School Falcons | 1-2-4 | vs | 3-5-6 | Marblehead High School Fishwagons | |
| 30 | | Greenwich Academy Gators | 2-3-4 | vs | 1-5-6 | Dartmouth High School Sailing | |
| 31 | | Darien High School Blue Wave | 2-3-5 | vs | 1-4-6 | East Greenwich High School Avengers | |
| 32 | | Greens Farms Academy Dragons | 1-2-3 | vs | 4-5-6 | St. Johns Prep Eagles | |
| 33 | | Fairfield Ludlowe High School Falcons | 3-5-6 | vs | 1-2-4 | Greenwich Academy Gators | |
| 34 | | East Greenwich High School Avengers | 1-2-4 | vs | 3-5-6 | Marblehead High School Fishwagons | |
| 35 | | St. Johns Prep Eagles | 3-4-5 | vs | 1-2-6 | Dartmouth High School Sailing | |
| 36 | | Greens Farms Academy Dragons | 2-3-4 | vs | 1-5-6 | Darien High School Blue Wave | |
| 37 | | Greenwich Academy Gators | 1-3-4 | vs | 2-5-6 | East Greenwich High School Avengers | |
| 38 | | Fairfield Ludlowe High School Falcons | 2-3-6 | vs | 1-4-5 | St. Johns Prep Eagles | |
| 39 | | Darien High School Blue Wave | 3-5-6 | vs | 1-2-4 | Marblehead High School Fishwagons | |
| 40 | | Greens Farms Academy Dragons | 1-5-6 | vs | 2-3-4 | Dartmouth High School Sailing | |
| 41 | | St. Johns Prep Eagles | 1-3-5 | vs | 2-4-6 | East Greenwich High School Avengers | |
| 42 | | Greenwich Academy Gators | 1-2-3 | vs | 4-5-6 | Darien High School Blue Wave | |
| 43 | | Dartmouth High School Sailing | 3-4-6 | vs | 1-2-5 | Fairfield Ludlowe High School Falcons | |
| 44 | | Greens Farms Academy Dragons | 1-4-5 | vs | 2-3-6 | Marblehead High School Fishwagons | |
| 45 | | Darien High School Blue Wave | 1-3-6 | vs | 2-4-5 | St. Johns Prep Eagles | |
| 46 | | East Greenwich High School Avengers | 2-3-4 | vs | 1-5-6 | Dartmouth High School Sailing | |
| 47 | | Marblehead High School Fishwagons | 3-4-6 | vs | 1-2-5 | Greenwich Academy Gators | |
| 48 | | Fairfield Ludlowe High School Falcons | 1-2-4 | vs | 3-5-6 | Greens Farms Academy Dragons | |
| 49 | | Dartmouth High School Sailing | 1-2-5 | vs | 3-4-6 | Darien High School Blue Wave | |
| 50 | | St. Johns Prep Eagles | 1-2-5 | vs | 3-4-6 | Marblehead High School Fishwagons | |
| 51 | | East Greenwich High School Avengers | 3-4-6 | vs | 1-2-5 | Fairfield Ludlowe High School Falcons | |
| 52 | | Greens Farms Academy Dragons | 3-4-5 | vs | 1-2-6 | Greenwich Academy Gators | |
| 53 | | Marblehead High School Fishwagons | 1-2-6 | vs | 3-4-5 | Dartmouth High School Sailing | |
| 54 | | Fairfield Ludlowe High School Falcons | 1-2-3 | vs | 4-5-6 | Darien High School Blue Wave | |
| 55 | | Greenwich Academy Gators | 1-2-3 | vs | 4-5-6 | St. Johns Prep Eagles | |
| 56 | | Greens Farms Academy Dragons | 2-4-6 | vs | 1-3-5 | East Greenwich High School Avengers | |
