| Game | Date & Time | Site | Sport & Level | Home | Away |
| 3473 | 9/27/2019 Fri 7:30 PM | Harrison County High School, Stadium | Football, Varsity | Harrison County HS | Boyd County HS |
| 3491 | 9/27/2019 Fri 7:30 PM | Lexington Catholic High School, Stadium | Football, Varsity | Lexington Catholic | Tates Creek HS |
| 3496 | 9/27/2019 Fri 7:30 PM | West Jessamine High School, Stadium | Football, Varsity | West Jessamine HS | East Jessamine HS |
| 3509 | 9/27/2019 Fri 7:30 PM | Madison Central High School, Stadium | Football, Varsity | Madison Central HS | Dixie Heights HS |
| 3523 | 9/27/2019 Fri 7:30 PM | Paris High School, Stadium | Football, Varsity | Paris High School | Eminence HS |
| 3536 | 9/27/2019 Fri 7:30 PM | Anderson County High School, Stadium | Football, Varsity | Anderson County HS | Lincoln County HS |
| 3559 | 9/27/2019 Fri 7:30 PM | Berea High School, Stadium | Football, Varsity | Berea Community HS | Sayre High School |
| 3468 | 9/27/2019 Fri 7:30 PM | Frederick Douglass High School, Stadium | Football, Varsity 7-Man | Frederick Douglass | Scott County HS |
| 3486 | 9/27/2019 Fri 7:30 PM | Boyle County High School, Stadium | Football, Varsity 7-Man | Boyle County HS | Highlands HS |
| 3514 | 9/27/2019 Fri 7:30 PM | Lexington Christian Academy, Stadium | Football, Varsity 7-Man | Lexington Christian | Williamsburg |
| 3531 | 9/27/2019 Fri 7:30 PM | Madison Southern High School, Stadium | Football, Varsity 7-Man | Madison Southern HS | Martha Layne Collins |
| 3542 | 9/27/2019 Fri 7:30 PM | George Rogers Clark HS (New Field), Stadium | Football, Varsity 7-Man | George Rogers Clark | Ballard High School |
| 3546 | 9/27/2019 Fri 7:30 PM | Great Crossing HS, Community Football Stadium | Football, Varsity 7-Man | Great Crossing HS | Paul Laurence Dunbar |
| 3553 | 9/27/2019 Fri 7:30 PM | Montgomery County High School, Stadium | Football, Varsity 7-Man | Montgomery County | Grant County HS |
