| Round 1 |
|---|
| 1 |  | Lane Tech College Prep Varsity | 1-2-4 | vs | 3-5-6 | Lyons Township High School Lions |  |
| 2 |  | Latin School of Chicago Romans | 1-2-3 | vs | 4-5-6 | Unregistered-MISSA Unregistered 1 |  |
| 3 |  | Walter Payton College Preparatory High School Grizzlies | 1-3-5 | vs | 2-4-6 | Unregistered-MISSA Unregistered 2 | |
| 4 |  | University of Chicago Laboratory Schools Maroons | 3-4-5 | vs | 1-2-6 | New Trier HS Trevian |  |
| 5 |  | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-2-4 | vs | 3-5-6 | Jones College Prep Eagles |  |
| 6 | | Latin School of Chicago Romans | 3-4-5 | vs | 1-2-6 DNF | Lane Tech College Prep Varsity | |
| 7 | | Walter Payton College Preparatory High School Grizzlies | 1-2-4 | vs | 3-5-6 | Lyons Township High School Lions | |
| 8 | | University of Chicago Laboratory Schools Maroons | 1-2-5 | vs | 3-4-6 | Unregistered-MISSA Unregistered 1 | |
| 9 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-2-4 | vs | 3-5-6 | Unregistered-MISSA Unregistered 2 | |
| 10 | | New Trier HS Trevian | 4-5-6 | vs | 1-2-3 | Jones College Prep Eagles | |
| 11 | | Walter Payton College Preparatory High School Grizzlies | 1-3-5 | vs | 2-4-6 | Latin School of Chicago Romans | |
| 12 | | University of Chicago Laboratory Schools Maroons | 1-2-4 | vs | 3-5-6 | Lane Tech College Prep Varsity | |
| 13 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-2-6 | vs | 3-4-5 | Lyons Township High School Lions | |
| 14 | | New Trier HS Trevian | 1-2-6 | vs | 3-4-5 | Unregistered-MISSA Unregistered 1 | |
| 15 | | Unregistered-MISSA Unregistered 2 | 3-4-5 | vs | 1-2-6 | Jones College Prep Eagles | |
| 16 | | University of Chicago Laboratory Schools Maroons | 4-5-6 | vs | 1-2-3 | Walter Payton College Preparatory High School Grizzlies | |
| 17 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-2-5 | vs | 3-4-6 | Latin School of Chicago Romans | |
| 18 | | New Trier HS Trevian | 1-2-4 | vs | 3-5-6 | Lane Tech College Prep Varsity | |
| 19 | | Unregistered-MISSA Unregistered 2 | 1-2-4 | vs | 3-5-6 | Lyons Township High School Lions | |
| 20 | | Unregistered-MISSA Unregistered 1 | 3-5-6 | vs | 1-2-4 | Jones College Prep Eagles | |
| 21 | | St. Ignatius College Prep, Chicago, IL Wolfpack | 1-4-6 | vs | 2-3-5 | University of Chicago Laboratory Schools Maroons | |
| 22 | | New Trier HS Trevian | 2-5-6 | vs | 1-3-4 | Walter Payton College Preparatory High School Grizzlies | |
| 23 | | Unregistered-MISSA Unregistered 2 | 1-3-6 | vs | 2-4-5 | Latin School of Chicago Romans | |
| 24 | | Unregistered-MISSA Unregistered 1 | | vs | | Lane Tech College Prep Varsity | |
| 25 | | Lyons Township High School Lions | | vs | | Jones College Prep Eagles | |
| 26 | | New Trier HS Trevian | | vs | | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 27 | | Unregistered-MISSA Unregistered 2 | | vs | | University of Chicago Laboratory Schools Maroons | |
| 28 | | Unregistered-MISSA Unregistered 1 | | vs | | Walter Payton College Preparatory High School Grizzlies | |
| 29 | | Lyons Township High School Lions | | vs | | Latin School of Chicago Romans | |
| 30 | | Lane Tech College Prep Varsity | | vs | | Jones College Prep Eagles | |
| 31 | | Unregistered-MISSA Unregistered 2 | | vs | | New Trier HS Trevian | |
| 32 | | Unregistered-MISSA Unregistered 1 | | vs | | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 33 | | Lyons Township High School Lions | | vs | | University of Chicago Laboratory Schools Maroons | |
| 34 | | Lane Tech College Prep Varsity | | vs | | Walter Payton College Preparatory High School Grizzlies | |
| 35 | | Latin School of Chicago Romans | | vs | | Jones College Prep Eagles | |
| 36 | | Unregistered-MISSA Unregistered 1 | | vs | | Unregistered-MISSA Unregistered 2 | |
| 37 | | Lyons Township High School Lions | | vs | | New Trier HS Trevian | |
| 38 | | Lane Tech College Prep Varsity | | vs | | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 39 | | Latin School of Chicago Romans | | vs | | University of Chicago Laboratory Schools Maroons | |
| 40 | | Walter Payton College Preparatory High School Grizzlies | | vs | | Jones College Prep Eagles | |
| 41 | | Lyons Township High School Lions | | vs | | Unregistered-MISSA Unregistered 1 | |
| 42 | | Lane Tech College Prep Varsity | | vs | | Unregistered-MISSA Unregistered 2 | |
| 43 | | Latin School of Chicago Romans | | vs | | New Trier HS Trevian | |
| 44 | | Walter Payton College Preparatory High School Grizzlies | | vs | | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 45 | | University of Chicago Laboratory Schools Maroons | | vs | | Jones College Prep Eagles | |
| Round 2 |
|---|
| 46 | | Unregistered-MISSA Unregistered 2 | | vs | | Jones College Prep Eagles | |
| 47 | | Unregistered-MISSA Unregistered 1 | | vs | | Lane Tech College Prep Varsity | |
| 48 | | University of Chicago Laboratory Schools Maroons | | vs | | Latin School of Chicago Romans | |
| 49 | | St. Ignatius College Prep, Chicago, IL Wolfpack | | vs | | Lyons Township High School Lions | |
| 50 | | New Trier HS Trevian | | vs | | Walter Payton College Preparatory High School Grizzlies | |
| 51 | | Unregistered-MISSA Unregistered 1 | | vs | | Unregistered-MISSA Unregistered 2 | |
| 52 | | University of Chicago Laboratory Schools Maroons | | vs | | Jones College Prep Eagles | |
| 53 | | St. Ignatius College Prep, Chicago, IL Wolfpack | | vs | | Lane Tech College Prep Varsity | |
| 54 | | New Trier HS Trevian | | vs | | Latin School of Chicago Romans | |
| 55 | | Lyons Township High School Lions | | vs | | Walter Payton College Preparatory High School Grizzlies | |
| 56 | | University of Chicago Laboratory Schools Maroons | | vs | | Unregistered-MISSA Unregistered 1 | |
| 57 | | St. Ignatius College Prep, Chicago, IL Wolfpack | | vs | | Unregistered-MISSA Unregistered 2 | |
| 58 | | New Trier HS Trevian | | vs | | Jones College Prep Eagles | |
| 59 | | Lyons Township High School Lions | | vs | | Lane Tech College Prep Varsity | |
| 60 | | Latin School of Chicago Romans | | vs | | Walter Payton College Preparatory High School Grizzlies | |
| 61 | | St. Ignatius College Prep, Chicago, IL Wolfpack | | vs | | University of Chicago Laboratory Schools Maroons | |
| 62 | | New Trier HS Trevian | | vs | | Unregistered-MISSA Unregistered 1 | |
| 63 | | Lyons Township High School Lions | | vs | | Unregistered-MISSA Unregistered 2 | |
| 64 | | Latin School of Chicago Romans | | vs | | Jones College Prep Eagles | |
| 65 | | Lane Tech College Prep Varsity | | vs | | Walter Payton College Preparatory High School Grizzlies | |
| 66 | | New Trier HS Trevian | | vs | | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 67 | | Lyons Township High School Lions | | vs | | University of Chicago Laboratory Schools Maroons | |
| 68 | | Latin School of Chicago Romans | | vs | | Unregistered-MISSA Unregistered 1 | |
| 69 | | Lane Tech College Prep Varsity | | vs | | Unregistered-MISSA Unregistered 2 | |
| 70 | | Jones College Prep Eagles | | vs | | Walter Payton College Preparatory High School Grizzlies | |
| 71 | | Lyons Township High School Lions | | vs | | New Trier HS Trevian | |
| 72 | | Latin School of Chicago Romans | | vs | | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 73 | | Lane Tech College Prep Varsity | | vs | | University of Chicago Laboratory Schools Maroons | |
| 74 | | Jones College Prep Eagles | | vs | | Unregistered-MISSA Unregistered 1 | |
| 75 | | Unregistered-MISSA Unregistered 2 | | vs | | Walter Payton College Preparatory High School Grizzlies | |
| 76 | | Latin School of Chicago Romans | | vs | | Lyons Township High School Lions | |
| 77 | | Lane Tech College Prep Varsity | | vs | | New Trier HS Trevian | |
| 78 | | Jones College Prep Eagles | | vs | | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 79 | | Unregistered-MISSA Unregistered 2 | | vs | | University of Chicago Laboratory Schools Maroons | |
| 80 | | Unregistered-MISSA Unregistered 1 | | vs | | Walter Payton College Preparatory High School Grizzlies | |
| 81 | | Lane Tech College Prep Varsity | | vs | | Latin School of Chicago Romans | |
| 82 | | Jones College Prep Eagles | | vs | | Lyons Township High School Lions | |
| 83 | | Unregistered-MISSA Unregistered 2 | | vs | | New Trier HS Trevian | |
| 84 | | Unregistered-MISSA Unregistered 1 | | vs | | St. Ignatius College Prep, Chicago, IL Wolfpack | |
| 85 | | University of Chicago Laboratory Schools Maroons | | vs | | Walter Payton College Preparatory High School Grizzlies | |
| 86 | | Jones College Prep Eagles | | vs | | Lane Tech College Prep Varsity | |
| 87 | | Unregistered-MISSA Unregistered 2 | | vs | | Latin School of Chicago Romans | |
| 88 | | Unregistered-MISSA Unregistered 1 | | vs | | Lyons Township High School Lions | |
| 89 | | University of Chicago Laboratory Schools Maroons | | vs | | New Trier HS Trevian | |
| 90 | | St. Ignatius College Prep, Chicago, IL Wolfpack | | vs | | Walter Payton College Preparatory High School Grizzlies | |
