| Round 1 |
|---|
| 1 |  | Tabor Academy Seawolves | 1-2-5 | vs | 3-4-6 | Archbishop Spalding Cavaliers |  |
| 2 |  | Saint Ignatius College Prep, Chicago, IL Wolfpack | 1-4-5 | vs | 2-3-6 | Fairfield Ludlowe High School Falcons |  |
| 3 |  | Sharon High School Varsity | 4-5-6 | vs | 1-2-3 | Greens Farms Academy Dragons |  |
| 4 |  | Olympia High School Bears | 3-4-5 | vs | 1-2-6 | Norfolk Academy Bulldogs |  |
| 5 |  | Norfolk Collegiate School Oaks | 1-2-6 | vs | 3-4-5 | University of Chicago Laboratory Schools Maroons |  |
| 6 | | Saint Ignatius College Prep, Chicago, IL Wolfpack | 1-5-6 | vs | 2-3-4 | Tabor Academy Seawolves | |
| 7 | | Sharon High School Varsity | 2-4-6 | vs | 1-3-5 | Archbishop Spalding Cavaliers | |
| 8 | | Olympia High School Bears | 2-5-6 | vs | 1-3-4 | Fairfield Ludlowe High School Falcons | |
| 9 | | Norfolk Collegiate School Oaks | 3-4-5 | vs | 1-2-6 | Greens Farms Academy Dragons | |
| 10 | | Norfolk Academy Bulldogs | 2-3-4 | vs | 1-5-6 | University of Chicago Laboratory Schools Maroons | |
| 11 | | Sharon High School Varsity | 3-4-6 | vs | 1-2-5 | Saint Ignatius College Prep, Chicago, IL Wolfpack | |
| 12 | | Olympia High School Bears | 4-5-6 | vs | 1-2-3 | Tabor Academy Seawolves | |
| 13 | | Norfolk Collegiate School Oaks | 1-2-4 | vs | 3-5-6 | Archbishop Spalding Cavaliers | |
| 14 | | Norfolk Academy Bulldogs | 3-4-6 | vs | 1-2-5 | Fairfield Ludlowe High School Falcons | |
| 15 | | Greens Farms Academy Dragons | 2-3-4 | vs | 1-5-6 | University of Chicago Laboratory Schools Maroons | |
| 16 | | Olympia High School Bears | 2-3-5 | vs | 1-4-6 | Sharon High School Varsity | |
| 17 | | Norfolk Collegiate School Oaks | 1-2-6 | vs | 3-4-5 | Saint Ignatius College Prep, Chicago, IL Wolfpack | |
| 18 | | Norfolk Academy Bulldogs | 3-4-6 | vs | 1-2-5 | Tabor Academy Seawolves | |
| 19 | | Greens Farms Academy Dragons | 3-5-6 | vs | 1-2-4 | Archbishop Spalding Cavaliers | |
| 20 | | Fairfield Ludlowe High School Falcons | 1-2-5 | vs | 3-4-6 | University of Chicago Laboratory Schools Maroons | |
| 21 | | Norfolk Collegiate School Oaks | 1-2-4 | vs | 3-5-6 | Olympia High School Bears | |
| 22 | | Norfolk Academy Bulldogs | 1-2-6 | vs | 3-4-5 | Sharon High School Varsity | |
| 23 | | Greens Farms Academy Dragons | 2-3-4 | vs | 1-5-6 | Saint Ignatius College Prep, Chicago, IL Wolfpack | |
| 24 | | Fairfield Ludlowe High School Falcons | 3-4-6 | vs | 1-2-5 | Tabor Academy Seawolves | |
| 25 | | Archbishop Spalding Cavaliers | 1-2-5 | vs | 3-4-6 | University of Chicago Laboratory Schools Maroons | |
| 26 | | Norfolk Academy Bulldogs | 1-3-4 | vs | 2-5-6 | Norfolk Collegiate School Oaks | |
| 27 | | Greens Farms Academy Dragons | 2-3-4 | vs | 1-5-6 | Olympia High School Bears | |
| 28 | | Fairfield Ludlowe High School Falcons | 1-2-3 | vs | 4-5-6 | Sharon High School Varsity | |
| 29 | | Archbishop Spalding Cavaliers | 1-2-3 | vs | 4-5-6 | Saint Ignatius College Prep, Chicago, IL Wolfpack | |
| 30 | | Tabor Academy Seawolves | 1-3-4 | vs | 2-5-6 | University of Chicago Laboratory Schools Maroons | |
| 31 | | Greens Farms Academy Dragons | 2-3-4 | vs | 1-5-6 | Norfolk Academy Bulldogs | |
| 32 | | Fairfield Ludlowe High School Falcons | 4-5-6 | vs | 1-2-3 | Norfolk Collegiate School Oaks | |
| 33 | | Archbishop Spalding Cavaliers | 1-2-5 | vs | 3-4-6 | Olympia High School Bears | |
| 34 | | Tabor Academy Seawolves | 1-2-3 | vs | 4-5-6 | Sharon High School Varsity | |
| 35 | | Saint Ignatius College Prep, Chicago, IL Wolfpack | 2-3-5 | vs | 1-4-6 | University of Chicago Laboratory Schools Maroons | |
| 36 | | Fairfield Ludlowe High School Falcons | 3-4-5 | vs | 1-2-6 | Greens Farms Academy Dragons | |
| 37 | | Archbishop Spalding Cavaliers | 1-2-5 | vs | 3-4-6 | Norfolk Academy Bulldogs | |
| 38 | | Tabor Academy Seawolves | 1-2-6 | vs | 3-4-5 | Norfolk Collegiate School Oaks | |
| 39 | | Saint Ignatius College Prep, Chicago, IL Wolfpack | 1-2-6 | vs | 3-4-5 | Olympia High School Bears | |
| 40 | | Sharon High School Varsity | 3-4-6 | vs | 1-2-5 | University of Chicago Laboratory Schools Maroons | |
| 41 | | Archbishop Spalding Cavaliers | 1-2-3 | vs | 4-5-6 | Fairfield Ludlowe High School Falcons | |
| 42 | | Tabor Academy Seawolves | 1-3-4 | vs | 2-5-6 | Greens Farms Academy Dragons | |
| 43 | | Saint Ignatius College Prep, Chicago, IL Wolfpack | 3-4-5 | vs | 1-2-6 | Norfolk Academy Bulldogs | |
| 44 | | Sharon High School Varsity | 2-5-6 | vs | 1-3-4 | Norfolk Collegiate School Oaks | |
| 45 | | Olympia High School Bears | 2-4-6 | vs | 1-3-5 | University of Chicago Laboratory Schools Maroons | |
