Highland 1999 Football (8-3)
8/27 A Fredericktown (3-7) [5:19] W 21-12
9/3 H Elgin (11-1) [4:14] L 7-12
9/10 A Cardington-Lincoln (2-8) [6:23] L 0-1 forfeit
9/17 H Buckeye Valley (7-3) [3:10] W 31-15
9/24 H Ridgedale (7-5) [6:23] W 35-12
10/1 A Mount Gilead (2-8) [5:20] W 42-0
10/8 A River Valley (5-5) [4:14] W 24-0
10/15 H North Union (4-6) [5:20] W 40-7
10/22 H Northmor (0-10) [5:20] W 55-0
10/29 A Pleasant (7-3) [5:20] W 53-20
11/6 A # Elgin (11-1) [4:14] L 13-21
# - Ohio playoff game