On Monday, Oct 19, 2009, the Chesapeake Varsity Boys Football team lost their game against Broadneck High School by a score of 0-44.
On Friday, Oct 2, 2009, the Chesapeake Varsity Boys Football team lost their game against Meade High School by a score of 0-22.
On Friday, Sep 25, 2009, the Chesapeake Varsity Boys Football team lost their game against Arundel High School by a score of 0-54.
On Thursday, Sep 17, 2009, the Chesapeake Varsity Boys Football team lost their game against North County High School by a score of 6-46.
On Friday, Sep 11, 2009, the Chesapeake Varsity Boys Football team lost their game against Northeast High School by a score of 3-19.