Unable to break into the Everton first-team, the following summer Henderson moved south to join Reading in the Southern League where he spent the next four years.
[1] He made his debut for the "Saints" playing at right-back in the opening match of the 1901–02 season, a 1–1 draw with New Brompton at The Dell.
Frustrated by the lack of regular first-team football, Henderson decided to return to Everton in the 1902 close season.
[1] Henderson made his Everton debut on 13 September 1902, replacing William Balmer in a 1–0 defeat to Newcastle United.
Henderson remained at Reading for two years, before returning to the Football League to join Clapton Orient in the Second Division in August 1906.