On Friday, Nov 17, 2023, the Headland Varsity Boys Football team won their game against UMS-Wright Prep High School by a score of 35-21.
 Tournament Game
2023 AHSAA Football Playoffs 5AOn Friday, Oct 27, 2023, the Headland Varsity Boys Football team won their game against New Brockton High School by a score of 42-20.
On Friday, Oct 13, 2023, the Headland Varsity Boys Football team won their game against Carroll High School by a score of 52-22.
On Friday, Oct 6, 2023, the Headland Varsity Boys Football team won their game against Greenville High School by a score of 36-12.
On Friday, Sep 15, 2023, the Headland Varsity Boys Football team won their game against Rehobeth High School by a score of 22-6.
On Friday, Sep 8, 2023, the Headland Varsity Boys Football team lost their game against Eufaula High School by a score of 14-56.
On Friday, Sep 1, 2023, the Headland Varsity Boys Football team won their game against Abbeville High School by a score of 38-8.
On Friday, Aug 25, 2023, the Headland Varsity Boys Football team won their game against Geneva High School by a score of 45-6.