| Date | School | Opponent | Time | |||
| 1-Oct | Bowling Green | 0 | vs | Capital City | 11 | Hickman Tourney |
| Bowling Green | 7 | vs | St. Francis Borgia | 2 | Hickman Tourney | |
| Elsberry | 6 | vs | Ft. Zumwalt East | 4 | ||
| 2-Oct | Bowling Green | 0 | vs | Blair Oaks | 2 | Hickman Tourney |
| Bowling Green | 4 | vs | Father Tolton | 0 | Hickman Tourney | |
| Clopton | 0 | vs | St. Charles | 3 | ||
| Elsberry | 12 | vs | St. Charles | 0 | ||
| Clopton | 1 | vs | Elsberry | 6 | ||
| Silex | @ | South Callaway Tournament | Cancelled | |||
| 4-Oct | Bowling Green | 4 | @ | Warrenton | 5 | |
| Elsberry | 6 | vs | Winfield | 1 | ||
| Louisiana | 3 | @ | South Shelby | 13 | ||
| Van-Far | vs | Marion County | Postponed | |||
| 5-Oct | Clopton | 0 | vs | Bowling Green | 10 | |
| Elsberry | 5 | vs | Montgomery County | 3 | ||
| Louisiana | 4 | vs | Community R-VI | 12 | ||
| Mark Twain | 1 | @ | North Callaway | 4 | ||
| Silex | 17 | @ | Wellsville-Middletown | 0 | ||
| Van-Far | 2 | vs | Wright City | 8 | ||
| 6-Oct | Clopton | vs | Monroe City | Cancelled | ||
| 7-Oct | Bowling Green | 8 | @ | North Callaway | 0 | |
| Clopton | vs | Van-Far | Postponed | |||
| Elsberry | 4 | vs | Silex | 2 | ||
| Louisiana | 2 | vs | Mark Twain | 9 | ||
| 8-Oct | Bowling Green | 0 | vs | Troy-Buchanan | 4 | |
| Clopton | 1 | @ | Canton | 4 | ||
| 11-Oct | Bowling Green | @ | Centralia | Cancelled | ||
| Louisiana | @ | Canton | Cancelled | |||
| Silex | vs | Hermann | Cancelled | |||
| Van-Far | 7 | @ | South Callaway | 17 | ||
| 12-Oct | Class 1 District 8 Softball – Opening Round | |||||
| (4) Clopton | 9 | vs | (5) New Haven | 0 | ||
| (3) Community R-VI | 11 | vs | (6)Wellsville-Middletown | 0 | 5 Innings | |
| Class 2 District 4 Softball – Opening Round | ||||||
| (2) Elsberry | 15 | vs | (7) Brentwood | 0 | ||
| (4) Jefferson (Fetus) | 15 | vs | (5) Hermann | 5 | ||
| (3) Bishop DuBourg | 15 | vs | (6) Gateway Science Charter | 0 | ||
| Class 3 District 6 Softball – Opening Round | ||||||
| (1) Hallsville | 9 | vs | (8) Wright City | 2 | ||
| (4) Centralia | 9 | vs | (5) Mexico | 14 | ||
| (2) Fulton | 10 | vs | (7) Moberly | 0 | ||
| (3) Bowling Green | 0 | vs | (6) Winfield | 2 | ||
| 13-Oct | Class 1 District 8 Softball – Semi-Finals | |||||
| (1) Silex | 2 | vs | (4) Clopton | 1 | ||
| (2) Van-Far | 6 | vs | (3) Community R-VI | 4 | ||
| Class 2 District 4 Softball – Semi-Finals | ||||||
| (1) Valley Park | 19 | vs | (4) Jefferson (Fetus) | 5 | ||
| (2) Elsberry | 8 | vs | (3) Bishop DuBourg | 0 | ||
| Class 3 District 6 Softball – Semi-Finals | ||||||
| (1) Hallsville | 13 | vs | (5) Mexico | 8 | ||
| (2) Fulton | 11 | vs | (6) Winfield | 1 | ||
| Class 2 District 5 Softball – Opening Round | ||||||
| (4) Clark County | vs | (5) South Shelby | Postponed | |||
| (2) Palmyra | vs | (7) Louisiana | Postponed | |||
| (3) Highland | vs | (6) Mark Twain | Postponed | |||
| 14-Oct | Class 2 District 5 Softball – Opening Round | |||||
| (4) Clark County | 10 | vs | (5) South Shelby | 4 | ||
| (2) Palmyra | 10 | vs | (7) Louisiana | 0 | 5 innings | |
| (3) Highland | 6 | vs | (6) Mark Twain | 0 | ||
| 15-Oct | Class 1 District 8 Softball – Championship | |||||
| (1) Silex | vs | (2) Van-Far | Postponed | |||
| Class 2 District 4 Softball – Semi-Finals | ||||||
| (1) Valley Park | vs | (2) Elsberry | Postponed | |||
| Class 3 District 6 Softball – Semi-Finals | ||||||
| (1) Hallsville | vs | (2) Fulton | Postponed | |||
| Class 2 District 5 Softball – Semi-Finals | ||||||
| (1) Monroe City | 2 | vs | (4) Clark County | 6 | ||
| (2) Palmyra | 1 | vs | (3) Highland | 3 | ||
| 16-Oct | Class 1 District 8 Softball – Championship | |||||
| (1) Silex | 14 | vs | (2) Van-Far | 4 | ||
| Class 2 District 4 Softball – Championship | ||||||
| (1) Valley Park | 1 | vs | (2) Elsberry | 11 | ||
| Class 2 District 5 Softball – Championship | ||||||
| (4) Clark County | 7 | vs | (3) Highland | 3 | ||
| Class 3 District 6 Softball – Championship | ||||||
| (1) Hallsville | 5 | vs | (2) Fulton | 12 | ||
| 20-Oct | Class 1 Sectionals @ Northeast (Cairo) | |||||
| Silex | 10 | @ | Cairo | 0 | ||
| Class 2 Quarterfinals @ New Bloomfield | ||||||
| Elsberry | 3 | @ | New Bloomfield | 7 | ||
| 23-Oct | Class 1 Sectionals @ Silex | |||||
| Silex | 3 | @ | St. Elizabeth | 7 | ||