| 5/1/21 | Bowling Green | 2 | vs | Hallsville | 3 | |
| Elsberry | 6 | @ | Hermann | 4 | ||
| 5/3/21 | Bowling Green | 9 | vs | Hannibal | 2 | |
| Louisiana | 5 | vs | Marion County | 4 | ||
| Mark Twain | 0 | vs | South Shelby | 16 | ||
| Silex | 3 | vs | Wellsville-Middletown | 4 | ||
| Van-Far | 0 | vs | Sturgeon | 14 | ||
| 5/4/21 | Bowling Green | 16 | vs | Canton | 2 | |
| Louisiana | 0 | @ | North Shelby | 2 | ||
| 5/5/21 | Elsberry | 6 | @ | Montgomery County | 6 | |
| Silex | 1 | @ | North Callaway | 6 | ||
| 5/6/21 | Louisiana | 5 | vs | Monroe City | 8 | |
| Mark Twain | 7 | vs | Community R-VI | 8 | ||
| Silex | 9 | vs | Elsberry | 6 | ||
| 5/7/21 | Bowling Green | 12 | vs | Warrenton | 11 | |
| Van-Far | 14 | @ | Monroe City | 15 | ||
| 5/10/21 | Louisiana | 2 | vs | Mark Twain | 9 | |
| Silex | @ | New Haven | Cancelled | |||
| 5/11/21 | Silex | 8 | vs | Bowling Green | 5 | |
| 5/13/21 | Van-Far | 1 | @ | Montgomery County | 17 | |
| 5/14/21 | Class 4 District 5 – Opening Round | |||||
| (5) Bowling Green | 9 | vs | (4) Orchard Farm | 6 | ||
| 5/15/21 | Class 3 District 5 – Opening Round | |||||
| (4) Mark Twain | vs | (5) Highland | V | Postponed | ||
| 5/17/21 | Class 2 District 10 – Opening Round | |||||
| (1) Louisiana | vs | (4) Van-Far | V | Postponed | ||
| (2) Paris | vs | (3) Silex | V | Postponed | ||
| Class 3 District 5 – Opening Round | ||||||
| (4) Mark Twain | vs | (5) Highland | V | Postponed | ||
| Class 3 District 6 – Semi-Finals | ||||||
| (2) Elsberry | vs | (3) Hermann | V | Postponed | ||
| Class 4 District 5 – Semi-Finals | ||||||
| (5) Bowling Green | vs | (1) St. Dominic | V | Postponed | ||
| 5/19/21 | Class 2 District 10 – Opening Round | |||||
| (1) Louisiana | 10 | vs | (4) Van-Far | 0 | ||
| (2) Paris | 3 | vs | (3) Silex | 6 | ||
| Class 3 District 6 – Semi-Finals | ||||||
| (2) Elsberry | 4 | vs | (3) Hermann | 3 | ||
| 5/20/21 | Class 2 District 10 – Championship | |||||
| (1) Louisiana | 2 | vs | (3) Silex | 12 | ||
| Class 3 District 5 – Opening Round | ||||||
| (4) Mark Twain | 4 | vs | (5) Highland | 5 | ||
| Class 3 District 6 – Championship | ||||||
| (2) Elsberry | 4 | vs | (5) Montgomery County | 1 | ||
| Class 4 District 5 – Semi-Finals | ||||||
| (5) Bowling Green | 0 | vs | (1) St. Dominic | 10 | ||
| 5/24/21 | Class 2 Sectionals | |||||
| Silex | 1 | @ | Eugene | 11 | ||
| 5/25/21 | Class 3 Sectionals | |||||
| Elsberry | 7 | @ | Maplewood-Richmond Heights | 3 | ||
| 5/27/21 | Class 3 Quarterfinals | |||||
| Elsberry | 6 | vs | Father Tolton | 4 | ||
| 6/2/21 | Class 3 Semifinals | |||||
| Elsberry | 0 | vs | Linn | 11 | ||
| 6/3/21 | Class 3 Third Place Game | |||||
| Elsberry | 5 | vs | Jefferson | 7 | ||
| Updated 06.03.21 | ||||||