After his death in 1937, Henderson left some of his considerable estate to family members, but most of his money was used to establish a perpetual trust to fund education and healthcare in Troy.

[2] The school's football team is in the 5A division of the AHSAA and participates in Region 2 (Southeast Alabama).

The school's football team won the state championship in the Fall of 1980 in the 3A division of the AHSAA.

There is a blue wall in left field that is similar to the "Green Monster" at Fenway Park.

In 2004, the Trojans won the 5A State Championship by defeating Cullman High School in best-of-three series.

CHHS is in the AHSAA record book for the following achievements:[6] •Third Most Homeruns in an Inning (4) vs. Brantley in 2011-Tripp Blackmon, Jalin Lawson, Chase Connell, and Gregory Barnette •Most Consecutive Homeruns (4) vs. Brantley in 2011-Blackmon, Lawson, Connell, and Barnette • Most and Third Most Times Hit By Pitches in a Game (9) vs. Bullock County in 2014 and (8) vs. LAMP in 2012 •Most Double Plays Turned in a Game (5) vs. Northview in 2012-Luke Hastings (3B), Michael Fox (SS), Jalin Lawson (2B), Joey Denison (1B) In 1992, Charles Henderson's Royce Emerson won an individual state championship after winning the #1-seed bracket in the 5A Alabama State Playoffs.

In 2003 and 2004, Josh Rogers won the district championships as the #1-seed, qualifying for the state playoffs where he would fall in the Second Round both years.

The Charles Henderson High School BEST Robotics team was first sponsored in 2010 by the physics teacher at the time.