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Born in Redhill, the central defender spent eight years at Chelsea prior to joining Swindon, where he won an FA Youth Cup winner's medal, but did not manage a first team league appearance.
Snapped up by Swindon in January 2017 after a loan at Aldershot was cut short, big things were expected after he signed a two and a half year deal to play at the County Ground - joining Chelsea loanees Charlie Colkett, Fankaty Dabo and Islam Feruz in the Town squad, he made his debut as a late substitute in a 1-0 defeat at Bristol Rovers the day after signing. By mid-March, he had claimed a regular starting spot - settling in well at the back and very comfortable on the ball - but his introduction was not enough to avoid the Town's relegation to League Two.
Conroy started the 2017/18 season as a key member of new manager David Flitcroft's squad - but his season came to an unfortunate end in mid-September, when he ruptured his anterior cruciate ligament in a 3-2 victory over Stevenage. By the time he returned the following season, Flitcroft had been replaced by Phil Brown - but Conroy was in and out of the side as he continued to struggle with fitness. It wasn't until the turn of the year that Conroy claimed a regular place in the starting eleven - by now under yet another new manager, Richie Wellens - and when Wellens dropped club captain Olly Lancashire toward the end of the season, Conroy was handed the armband in his absence. After netting his first Town goal in a 4-0 victory over Morecambe, though he was widely expected to leave the club at the end of the season, Conroy signed a one-year extension, and was named as the new club captain for the 2019/20 season, after Lancashire departed.
Unfortunately, it was another injury-hit campaign for Conroy - after a good start to the season that saw the Town challenging at the top of the table, Conroy suffered another cruciate ligament injury against Newport in September 2019. The injury kept him out for the whole campaign - in his absence, the Town secured the League Two title in a season curtailed by a global pandemic that prevented Conroy from making a return. Over the summer, Conroy signed another extension to his deal, while boss Wellens called for him to do more in the dressing room, following the departure of a number of experienced players.
Just as he appeared to be ready for a return, Conroy picked up a heel injury that required surgery in a pre-season friendly at Bristol City - by the time he returned to action in December 2020, Wellens had left the club to be replaced by John Sheridan, and the Town were in the midst of a relegation battle. He was soon back as a first choice - a place that he kept right through to the middle of March, despite a red card in a crucial bottom-of-the-table clash against Wigan in February that the Town held on to win 1-0 - the decision later being overturned. Suddenly though, Conroy found himself out of the squad altogether, after Sheridan made a unique quintuple substitution, seemingly to make a point with the Town 3-1 down at home to Gillingham - the Town boss later publicly accusing the Town captain of lacking fitness.
date of birth