[5] He scored some vital goals at the Croft ground, helping Haverhill reach the FA Cup Fourth Qualifying Round for the first time in their 125-year history during the 2006–07 campaign, before the minnows finally bowed out to Aldershot Town.

[10] He became a fan favourite at Spytty Park and he fired nine goals in 35 appearances during his first season with the Exiles, the 2009–10 campaign, as Newport won the Conference South title with a record 103 points.

[11] Playing at Conference Premier level for the first time in his career, Henry was again a key figure for Newport County during the 2010–11 campaign as the Exiles were the surprise package in the league and play-off contenders in the first half of the season.

After scoring at Kenilworth Road for Newport County in a 1–1 draw on 24 August 2010[12] he was on the radar of Luton manager Richard Money, who had already been impressed with Henry after spotting him in a pre-season match against Stevenage.

On 26 November 2010, Henry signed for Luton, initially on loan,[13] before making the move permanent on 5 January 2011,[14] returning to Kenilworth Road nine years after being released as a 15-year-old.

[16] However, a detached ligament in his foot sustained whilst playing for Newport County proved more serious than initially thought by the Luton Town medical staff, and Henry was sidelined for the remainder of the 2010–11 season with an injury that manager Richard Money described as "one in a million".

After a stint in New Zealand's ASB Premiership for Team Wellington, Henry signed for Dunstable Town in the summer of 2014 following their promotion for the Southern Premier Division.

[21] Henry's form with Newport County in 2010 earned him a call-up in the England national football C team, where he made his debut in a 2–2 draw with Wales.