| Date | Location | Result | |
| Nov 03, 2023 | Lexington, Ky. | FREDERICK DOUGLASS 48, HENRY CLAY 0 | Box score |
| Oct 27, 2023 | Somerset KY | Southwestern 45, HENRY CLAY 8 | Box score |
| Oct 20, 2023 | Lexington, KY | TATES CREEK 35, HENRY CLAY 6 | Box score |
| Oct 13, 2023 | Lexington KY | Paul Laurence Dunbar 32, HENRY CLAY 0 | Box score |
| Oct 06, 2023 | Lexington, Ky. | LAFAYETTE 30, HENRY CLAY 0 | Box score |
| Sep 29, 2023 | LEXINGTON, KY | BRYAN STATION 56, HENRY CLAY 0 | Box score |
| Sep 15, 2023 | Madison Southern | MADISON SOUTHERN 36, HENRY CLAY 6 | Box score |
| Sep 08, 2023 | Unknown | GEORGE ROGERS CLARK 48, HENRY CLAY 27 | Box score |
| Sep 01, 2023 | Lexington, Ky. | GREAT CROSSING 41, HENRY CLAY 0 | Box score |
| Aug 25, 2023 | Union KY | Cooper Jaguars 42, HENRY CLAY 2 | Box score |
| Aug 18, 2023 | HENRY CLAY HS | FLEMING COUNTY 20, HENRY CLAY 18 | Box score |