[11] In September 2012, Henderson went on a three-month loan to Coventry City,[12] making his debut in a 2–1 home defeat to Carlisle United.
[citation needed] After impressing manager Steve Bruce during two reserve matches, Henderson was signed by Hull City on 24 September 2013 on a free transfer and was given the number 30 shirt.
[15] Henderson made his debut against Huddersfield Town in the third round of the Football League Cup and came on in the 74th minute, replacing fellow Irish midfielder Stephen Quinn in a 1–0 win for the Tigers.
[23] Nevertheless, Henderson remained in the first team, until an ankle injury in the 2–2 draw against Milton Keynes Dons kept him out for the remainder of the season.
[25] On 25 November 2015, Henderson joined National League side Grimsby Town, on loan until January 2016.
[26] Having previously spending a week on trial at Scottish Premiership side Inverness Caledonian Thistle.
[32] Henderson made his return for Crawley, in a FA Cup replay at Bristol Rovers on 16 November as an emergency left back.
[35] Following his release from Crawley, Henderson joined National League South side Eastbourne Borough.
[36] On 14 August 2017, following a successful trial period, Henderson signed a one-year contract with Bulgarian club Pirin Blagoevgrad.