| Round 1 |
|---|
| 1 |  | Minnetonka High School Skippers | 1-2-4 | vs | 3-5-6 | New Trier HS Trevian |  |
| 2 |  | Lincoln Park High School Varsity | 1-2-4 | vs | 3-5-6 | St. Ignatius College Prep, Chicago, IL Wolfpack |  |
| 3 |  | University of Chicago Laboratory Schools Maroons | 3-4-6 | vs | 1-2-5 | Latin School of Chicago Romans |  |
| 4 |  | Jones College Prep Eagles | 1-2-4 | vs | 3-5-6 | Walter Payton College Preparatory High School Grizzlies |  |
| 5 | | Minnetonka High School Skippers | 2-5-6 | vs | 1-3-4 | Lincoln Park High School Varsity | |
| 6 | | Latin School of Chicago Romans | 2-3-4 | vs | 1-5-6 | New Trier HS Trevian | |
| 7 | | Walter Payton College Preparatory High School Grizzlies | 3-5-6 | vs | 1-2-4 | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 8 | | Jones College Prep Eagles | 3-5-6 | vs | 1-2-4 | University of Chicago Laboratory Schools Maroons | |
| 9 | | Lincoln Park High School Varsity | 1-2-6 | vs | 3-4-5 | Latin School of Chicago Romans | |
| 10 | | Minnetonka High School Skippers | 1-3-6 | vs | 2-4-5 | Walter Payton College Preparatory High School Grizzlies | |
| 11 | | University of Chicago Laboratory Schools Maroons | 3-5-6 | vs | 1-2-4 | New Trier HS Trevian | |
| 12 | | Jones College Prep Eagles | 2-5-6 | vs | 1-3-4 | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 13 | | Walter Payton College Preparatory High School Grizzlies | 2-4-6 | vs | 1-3-5 | Latin School of Chicago Romans | |
| 14 | | Lincoln Park High School Varsity | 3-5-6 | vs | 1-2-4 | University of Chicago Laboratory Schools Maroons | |
| 15 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-2-6 | vs | 3-4-5 | Minnetonka High School Skippers | |
| 16 | | Jones College Prep Eagles | 1-3-6 | vs | 2-4-5 | New Trier HS Trevian | |
| 17 | | University of Chicago Laboratory Schools Maroons | 1-2-3 | vs | 4-5-6 | Walter Payton College Preparatory High School Grizzlies | |
| 18 | | Latin School of Chicago Romans | 4-5-6 | vs | 1-2-3 | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 19 | | New Trier HS Trevian | 2-4-5 | vs | 1-3-6 | Lincoln Park High School Varsity | |
| 20 | | Minnetonka High School Skippers | 1-2-4 | vs | 3-5-6 | Jones College Prep Eagles | |
| 21 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 2-3-4 | vs | 1-5-6 | University of Chicago Laboratory Schools Maroons | |
| 22 | | Walter Payton College Preparatory High School Grizzlies | 3-4-6 | vs | 1-2-5 | New Trier HS Trevian | |
| 23 | | Latin School of Chicago Romans | 1-3-5 | vs | 2-4-6 | Minnetonka High School Skippers | |
| 24 | | Jones College Prep Eagles | 1-4-6 | vs | 2-3-5 | Lincoln Park High School Varsity | |
| 25 | | New Trier HS Trevian | 1-4-6 | vs | 2-3-5 | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 26 | | Minnetonka High School Skippers | 1-2-5 | vs | 3-4-6 | University of Chicago Laboratory Schools Maroons | |
| 27 | | Lincoln Park High School Varsity | 3-4-5 | vs | 1-2-6 | Walter Payton College Preparatory High School Grizzlies | |
| 28 | | Jones College Prep Eagles | 1-2-6 | vs | 3-4-5 | Latin School of Chicago Romans | |
