|view Gladwin's match-by-match record|
Gladwin arrived from Marlow in November 2013 having done the rounds in the Non-League scene - he previously been a member of the youth set-up at Reading.
His first season at Swindon was one of finding his feet in the professional game, making sixteen appearances without ever really standing out but started the 2014/15 campaign in the starting eleven in an attacking midfield role sitting just behind Michael Smith. Gladwin seemed expendable throughout the first half of the new season, either finding himself substituted or himself coming on but his growing worth within the squad was becoming more and more apparent. His first league goal was a winner against Fleetwood Town, heading in a Harry Toffolo cross, with just four minutes remaining.
In April 2015, with his gliding, effortless style, Gladwin seemingly became one of the most formidable players in the division. It started with a hat-trick in the 4-2 away win at Rochdale and a brace (both penalties) followed in a 3-3 draw against Walsall. His place in the starting eleven was firmly secured by the time the Play-Off Semi-Finals against Sheffield United had arrived. The first leg at Bramall Lane was a hard-fought encounter with Kieron Freeman putting the Blades ahead before Nathan Byrne was tripped in the box much to the disdain of the hosts. It was Gladwin who stepped up but his effort was well saved by Mark Howard much to the delight of the furious home fans. Despite this, Town equalised through a Sam Ricketts header, and then grabbed a last-gasp winner courtesy of Nathan Byrne to take a goal advantage to the County Ground.
The second leg would go down as one of the most entertaining games in modern Town history and Gladwin played a major part in this thanks to his glorious rasping fourth minute half-volley to put Town 1-0 up and then following it up with second, this time a tap-in, minutes later. The rollercoaster game finished 5-5 with Town going through 7-6 on aggregate.
Unfortunately, Swindon would go on to be utterly humiliated by Preston North End - losing 4-0 at Wembley in the Final, Gladwin was one of several players who failed to get a look-in. He was replaced for Louis Thompson with over 30 minutes left to play.
Despite the disastrous performance by Town, the squad was ripped apart in the transfer market with Gladwin and Massimo Luongo both joining Queens Park Rangers for an undisclosed fee, less than a week after the Wembley loss.
Gladwin struggled for gametime in the Championship with QPR and returned to Swindon on loan in October 2015, less than 5 months after leaving the club. He played 13 times, scoring twice during this spell. Although he showed glimpses, Gladwin struggled to rediscover the form that earned him a move away in the first place. He was then sent out on loan to Bristol City where he played once before getting injured.
In January 2017, Gladwin re-joined Swindon for a second time as Town desperately tried to find a way out of the relegation zone. By this point, however, injuries seemed to have taken its toll on Gladwin who really struggled to make a major impact in what was a poor Swindon side. He played 18 times, scoring twice, as Town were relegated to League Two.
Shortly afterwards, Gladwin joined Blackburn Rovers where his progress was severely halted by further injuries. In 2020, he joined Milton Keynes Dons where he was reunited with former Town coach, Luke Williams.
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