| Game | Date & Time | Site | Sport & Level | Home | Away |
| 3488 | 8/30/2019 Fri 6:00 PM | Lexington Catholic High School, Stadium | Football, Varsity 7-Man | Henry Clay | St. Xavier |
| 3865 | 8/30/2019 Fri 7:30 PM | Toyota Stadium Field, Toyota Stadium Field | Football, Varsity 7-Man | Paintsville | Beechwood |
| 3484 | 8/30/2019 Fri 7:30 PM | Frederick Douglass High School, Stadium | Football, Varsity | Frederick Douglass… | Tates Creek HS |
| 3494 | 8/30/2019 Fri 7:30 PM | West Jessamine High School, Stadium | Football, Varsity | West Jessamine HS | Bryan Station HS |
| 3529 | 8/30/2019 Fri 7:30 PM | Madison Southern High School, Stadium | Football, Varsity | Madison Southern HS | Southwestern |
| 3534 | 8/30/2019 Fri 7:30 PM | Anderson County High School, Stadium | Football, Varsity | Anderson County HS | Madison Central HS |
| 3551 | 8/30/2019 Fri 7:30 PM | Montgomery County High School, Stadium | Football, Varsity | Montgomery County HS | Somerset High |
| 3894 | 8/30/2019 Fri 7:30 PM | Bracken County High School, Stadium | Football, Varsity | Bracken County HS | Ludlow High School |
| 3896 | 8/30/2019 Fri 7:30 PM | Marion Country High School, Stadium | Football, Varsity | Marion County HS | Garrard County HS |
| 3444 | 8/30/2019 Fri 7:30 PM | Lafayette High School, Stadium | Football, Varsity 7-Man | Lafayette HS | Scott County HS |
| 3454 | 8/30/2019 Fri 7:30 PM | Franklin County, Stadium | Football, Varsity 7-Man | Franklin County HS | Western Hills HS |
| 3489 | 8/30/2019 Fri 8:40 PM | Lexington Catholic High School, Stadium | Football, Varsity 7-Man | Lexington Catholic HS | T.C. Howe |
| Game | Date & Time | Site | Sport & Level | Home | Away |
| 3871 | 8/31/2019 Sat 9:00 AM | Hayes Middle School, Football Field | Football, 6th | Edythe Jones Hayes MS | East Jessamine MS |
| 3876 | 8/31/2019 Sat 10:00 AM | Woodford County Middle School, Football Field | Football, 7th – 8th Doubleheader (4 – Man) | Woodford County MS | Jessie Clark MS |
| 3878 | 8/31/2019 Sat 10:00 AM | Elkhorn Middle School, Franklin County H.S. | Football, 7th – 8th Doubleheader (4 – Man) | Elkhorn MS | Bondurant MS |
| 3909 | 8/31/2019 Sat 12:30 PM | Lexington Catholic High School, Stadium | Football, 7th – 8th Doubleheader (4 – Man) | Lexington Catholic… | Highlands Blue |
| 3465 | 8/31/2019 Sat 5:00 PM | Boyle County High School, Stadium | Football, Varsity 7-Man | Mercer County HS | Allen County-scottville HS |
| 3419 | 8/31/2019 Sat 6:00 PM | Bourbon County High School, Stadium | Football, Varsity 7-Man | Frankfort HS | Paris High School |
| 3466 | 8/31/2019 Sat 8:00 PM | Boyle County High School, Stadium | Football, Varsity 7-Man | Boyle County HS | Bullitt Central HS |
| 3459 | 8/31/2019 Sat 8:45 PM | Bourbon County High School, Stadium | Football, Varsity 7-Man | Bourbon County HS | Letcher County Central |
