On Friday, Nov 5, 2021, the Chipley Varsity Boys Football team won their game against Jay High School by a score of 39-0.
On Friday, Oct 29, 2021, the Chipley Varsity Boys Football team lost their game against Walton High School by a score of 20-21.
On Thursday, Oct 21, 2021, the Chipley Varsity Boys Football team won their game against Lighthouse Private Christian Academy High School by a score of 31-13.
On Friday, Sep 17, 2021, the Chipley Varsity Boys Football team won their game against Vernon High School by a score of 50-0.
On Friday, Aug 27, 2021, the Chipley Varsity Boys Football team won their game against Graceville High School by a score of 47-0.