| Game | Date & Time | Site | Sport & Level | Home | Away |
| 3485 | 9/20/2019 Fri 6:30 PM | Frederick Douglass High School, Stadium | Football, Varsity | Frederick Douglass HS | Henry Clay HS |
| 3394 | 9/20/2019 Fri 6:30 PM | Tates Creek High School, Stadium | Football, Varsity | Tates Creek High School | Bryan Station HS |
| 3428 | 9/20/2019 Fri 7:00 PM | East Jessamine High School, Stadium | Football, Varsity | East Jessamine HS | Great Crossing HS |
| 3439 | 9/20/2019 Fri 7:30 PM | Paul Laurence Dunbar High School, Stadium | Football, Varsity | Paul Laurence Dunbar | West Jessamine HS |
| 3446 | 9/20/2019 Fri 7:30 PM | Lafayette High School, Stadium | Football, Varsity | Lafayette High School | Madison Central HS |
| 3450 | 9/20/2019 Fri 7:30 PM | Nicholas County High School, Stadium | Football, Varsity | Nicholas County HS | Morgan County HS |
| 3461 | 9/20/2019 Fri 7:30 PM | Bourbon County High School, Stadium | Football, Varsity | Bourbon County HS | Knox Central HS |
| 3467 | 9/20/2019 Fri 7:30 PM | Boyle County High School, Stadium | Football, Varsity | Boyle County HS | Christian Academy |
| 3479 | 9/20/2019 Fri 7:30 PM | Western Hills High School (Frankfort, KY), Stadium | Football, Varsity | Western Hills HS | Frankfort HS |
| 3513 | 9/20/2019 Fri 7:30 PM | Lexington Christian Academy, Stadium | Football, Varsity | Lexington Christian | Lexington Catholic |
| 3539 | 9/20/2019 Fri 7:30 PM | Berea High School, Stadium | Football, Varsity | Berea Community HS | Jenkins HS |
| 3541 | 9/20/2019 Fri 7:30 PM | George Rogers Clark High School, Stadium | Football, Varsity | George Rogers Clark | Southwestern |
| 3563 | 9/20/2019 Fri 7:30 PM | Anderson County High School, Stadium | Football, Varsity | Anderson County HS | Henderson County HS |
| 3921 | 9/20/2019 Fri 7:30 PM | Danville High School, Stadium | Football, Varsity | Danville HS | Hazard High School |
| 3402 | 9/20/2019 Fri 7:30 PM | Woodford County High School, Stadium | Football, Varsity | Woodford County HS | Franklin County HS |
| 3415 | 9/20/2019 Fri 7:30 PM | Scott County High School, Community Football Stadium | Football, Varsity | Scott County HS | Emmerich Manual |
| 3389 | 9/20/2019 Fri 7:30 PM | Mercer County High School, Alvis Johnson Field | Football, Varsity | Mercer County HS | Garrard County HS |
