| Date & Time | Site | Home | Away | Sport & Level |
| 8/23/2019 Fri 6:00 PM | East Jessamine High School, Stadium | East Jessamine HS | Franklin County HS | Football, Varsity |
| 8/23/2019 Fri 6:00 PM | Lafayette High School, Stadium | Lafayette HS | Johnson Central HS | Football, Varsity 7-Man |
| 8/23/2019 Fri 7:00 PM | Paris High School, Stadium | Paris High School | Fort Knox High School | Football, Varsity |
| 8/23/2019 Fri 7:30 PM | Paul Laurence Dunbar High School, Stadium | Paul Laurence Dunbar | North Laurel HS | Football, Varsity 7-Man |
| 8/23/2019 Fri 7:30 PM | Frederick Douglass High School, Stadium | Frederick Douglass HS | Bryan Station HS | Football, Varsity 7-Man |
| 8/23/2019 Fri 7:30 PM | Nicholas County High School, Stadium | Nicholas County HS | Fleming County HS | Football, Varsity |
| 8/23/2019 Fri 7:30 PM | Harrison County High School, Stadium | Harrison County HS | Newport High School | Football, Varsity |
| 8/23/2019 Fri 7:30 PM | Lexington Christian Academy, Stadium | Lexington Christian | Moore Traditional | Football, Varsity 7-Man |
| 8/23/2019 Fri 7:30 PM | Scott County High School, Community Football Stadium | Scott County HS | Great Crossing HS | Football, Varsity 7-Man |
| 8/23/2019 Fri 7:30 PM | Frankfort High School, Stadium | Frankfort High School | Lynn Camp | Football, Varsity |
| 8/23/2019 Fri 8:45 PM | East Jessamine High School, Stadium | West Jessamine HS | Bourbon County HS | Football, Varsity |
| 8/23/2019 Fri 8:45 PM | Lafayette High School, Stadium | Henry Clay | Simon Kenton HS | Football, Varsity 7-Man |
| Date & Time | Site | Home | Away | Sport & Level |
| 8/24/2019 Sat 10:00 AM | Lincoln County Middle School, Lincoln County HS | Lincoln County MS | Kenneth D. King MS | Football, 7th – 8th Doubleheader (4 – Man) |
| 8/24/2019 Sat 11:00 AM | Lexington Christian Academy, Stadium | Lexington Christian MS | Highlands Middle School | Football, 8th |
| 8/24/2019 Sat 2:00 PM | Clark Moores Middle School, @ Caudill Middle School | Clark Moores MS | Conner Middle School | Football, 7th – 8th Doubleheader (4 – Man) |
| 8/24/2019 Sat 5:00 PM | Mercer County High School, Alvis Johnson Field | Boyle County HS | Iroquois | Football, Varsity 7-Man |
| 8/24/2019 Sat 5:00 PM | Montgomery County High School, Stadium | South Laurel HS | Boyd County HS | Football, Varsity 7-Man |
| 8/24/2019 Sat 5:30 PM | Danville High School, Stadium | Bell County HS | Martha Layne Collins HS | Football, Varsity 7-Man |
| 8/24/2019 Sat 5:30 PM | Madison Central High School, Stadium | Madison Southern HS | Tates Creek HS | Football, Varsity 7-Man |
| 8/24/2019 Sat 6:00 PM | Lexington Christian Academy, Stadium | Lexington Christian JV | Woodford County JV | Football, JV |
| 8/24/2019 Sat 6:00 PM | Woodford County Middle School, Falling Springs (Turf) | Woodford County MS | Southern MS | Football, 7th – 8th Doubleheader (4 – Man) |
| 8/24/2019 Sat 8:00 PM | Mercer County High School, Alvis Johnson Field | Mercer County HS | West Carter HS | Football, Varsity 7-Man |
| 8/24/2019 Sat 8:00 PM | Montgomery County High School, Stadium | Montgomery County HS | Powell County | Football, Varsity 7-Man |
| 8/24/2019 Sat 8:10 PM | Madison Central High School, Stadium | Madison Central HS | Conner High School | Football, Varsity 7-Man |
| 8/24/2019 Sat 8:15 PM | Danville High School, Stadium | Danville High School | John Hardin HS | Football, Varsity 7-Man |