| Round 1 |
|---|
| 1 |  | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-4-6 | vs | 2-3-5 | University of Chicago Laboratory Schools Maroons |  |
| 2 |  | New Trier HS Trevian | 1-2-4 | vs | 3-5-6 | Walter Payton College Preparatory High School Grizzlies |  |
| 3 |  | Evanston Township HS Wildkits | 1-2-3 | vs | 4-5-6 | Loyola Academy Ramblers |  |
| 4 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-2-6 | vs | 3-4-5 | Latin School of Chicago Romans |  |
| 5 | | University of Chicago Laboratory Schools Maroons | 4-5-6 | vs | 1-2-3 | New Trier HS Trevian | |
| 6 | | Walter Payton College Preparatory High School Grizzlies | 1-3-6 | vs | 2-4-5 | Evanston Township HS Wildkits | |
| 7 | | Loyola Academy Ramblers | 3-4-6 | vs | 1-2-5 | Latin School of Chicago Romans | |
| 8 | | New Trier HS Trevian | 1-2-4 | vs | 3-5-6 | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 9 | | Evanston Township HS Wildkits | 1-2-5 | vs | 3-4-6 | University of Chicago Laboratory Schools Maroons | |
| 10 | | Walter Payton College Preparatory High School Grizzlies | 1-2-5 | vs | 3-4-6 | Loyola Academy Ramblers | |
| 11 | | New Trier HS Trevian | 1-2-5 | vs | 3-4-6 | Latin School of Chicago Romans | |
| 12 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-2-6 | vs | 3-4-5 | Evanston Township HS Wildkits | |
| 13 | | Loyola Academy Ramblers | 3-5-6 | vs | 1-2-4 | University of Chicago Laboratory Schools Maroons | |
| 14 | | Walter Payton College Preparatory High School Grizzlies | 1-5-6 | vs | 2-3-4 | Latin School of Chicago Romans | |
| 15 | | Evanston Township HS Wildkits | 3-5-6 DNS | vs | 1-2-4 | New Trier HS Trevian | |
| 16 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-2-4 | vs | 3-5-6 | Loyola Academy Ramblers | |
| 17 | | University of Chicago Laboratory Schools Maroons | 2-5-6 | vs | 1-3-4 | Walter Payton College Preparatory High School Grizzlies | |
| 18 | | Evanston Township HS Wildkits | 3-4-6 | vs | 1-2-5 | Latin School of Chicago Romans | |
| 19 | | Loyola Academy Ramblers | 4-5-6 | vs | 1-2-3 | New Trier HS Trevian | |
| 20 | | Walter Payton College Preparatory High School Grizzlies | 2-3-5 | vs | 1-4-6 | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 21 | | University of Chicago Laboratory Schools Maroons | 3-4-6 | vs | 1-2-5 | Latin School of Chicago Romans | |
| Round 2 |
|---|
| 22 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 2-3-6 | vs | 1-4-5 | University of Chicago Laboratory Schools Maroons | |
| 23 | | New Trier HS Trevian | 1-2-3 | vs | 4-5-6 | Walter Payton College Preparatory High School Grizzlies | |
| 24 | | Evanston Township HS Wildkits | 1-2-3 | vs | 4-5-6 DNS | Loyola Academy Ramblers | |
| 25 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-5-6 | vs | 2-3-4 | Latin School of Chicago Romans | |
| 26 | | University of Chicago Laboratory Schools Maroons | 3-4-5 | vs | 1-2-6 | New Trier HS Trevian | |
| 27 | | Walter Payton College Preparatory High School Grizzlies | 2-3-5 | vs | 1-4-6 | Evanston Township HS Wildkits | |
| 28 | | Loyola Academy Ramblers | 3-4-6 | vs | 1-2-5 | Latin School of Chicago Romans | |
| 29 | | New Trier HS Trevian | 1-2-4 | vs | 3-5-6 | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 30 | | Evanston Township HS Wildkits | 4-5-6 DNF | vs | 1-2-3 | University of Chicago Laboratory Schools Maroons | |
| 31 | | Walter Payton College Preparatory High School Grizzlies | 1-3-5 | vs | 2-4-6 | Loyola Academy Ramblers | |
| 32 | | New Trier HS Trevian | 1-2-4 | vs | 3-5-6 | Latin School of Chicago Romans | |
| 33 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-2-3 | vs | 4-5-6 | Evanston Township HS Wildkits | |
| 34 | | Loyola Academy Ramblers | 3-5-6 | vs | 1-2-4 | University of Chicago Laboratory Schools Maroons | |
| 35 | | Walter Payton College Preparatory High School Grizzlies | 2-4-6 | vs | 1-3-5 | Latin School of Chicago Romans | |
| 36 | | Evanston Township HS Wildkits | 3-5-6 | vs | 1-2-4 | New Trier HS Trevian | |
| 37 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-2-3 | vs | 4-5-6 | Loyola Academy Ramblers | |
| 38 | | University of Chicago Laboratory Schools Maroons | 2-5-6 | vs | 1-3-4 | Walter Payton College Preparatory High School Grizzlies | |
| 39 | | Evanston Township HS Wildkits | 1-5-6 | vs | 2-3-4 | Latin School of Chicago Romans | |
| 40 | | Loyola Academy Ramblers | 3-5-6 DNF | vs | 1-2-4 | New Trier HS Trevian | |
| 41 | | Walter Payton College Preparatory High School Grizzlies | 1-3-6 | vs | 2-4-5 | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 42 | | University of Chicago Laboratory Schools Maroons | 3-5-6 | vs | 1-2-4 | Latin School of Chicago Romans | |
