[5] He played the entire 2004 season with Vermont and was promoted to the Class A Savannah Sand Gnats of the South Atlantic League in 2005.

[6] He pitched three games at Triple-A Iowa before a shoulder injury ended his season and resulted in his release from the Cubs organization in March 2009.

[5] After ten years in the minors, Henderson earned his first promotion to MLB when the Milwaukee Brewers summoned him from Nashville on July 26, 2012, making his major league debut that night against the Washington Nationals, pitching one inning and striking out the first batter he faced, Roger Bernadina.

[4] Henderson was later transferred to the 60-day DL following a minor league rehab assignment,[6] and he ended up missing the rest of the season after having shoulder surgery in August.

Still seeking to reclaim his lost velocity after his 2014 shoulder surgery, Henderson was outrighted to the Triple-A Colorado Springs Sky Sox on May 21, 2015.

[6] Henderson signed a minor league contract with the New York Mets for 2015 that included an invitation to spring training.

[6][12] Henderson signed a minor league contract with the Chicago Cubs for 2017 with an invitation to spring training,[13] but he was released before the season's start.

[16] Before the cancellation of the 2020 minor league season, he was slated to be the pitching coach for the Brewers' Triple-A San Antonio Missions.

[17] Henderson was a member of the gold medal winning Canadian national baseball team at the 2011 Pan American Games.