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A huge defender signed on a two-and-a-half year deal from non-league outfit Alfreton Town in January 2011, for a fee believed to be in the region of £150,000 - a club record for the non-league side - Swindon beating off competition from Colchester, Luton and Derby for his signature. Flint made his Town debut in a 1-1 draw with Rochdale at the beginning of February, giving a promising performance on his Football League bow.
Though he started again three days later in a 3-0 defeat at Leyton Orient, he was back on the bench the following weekend - manager Danny Wilson perhaps unwilling to risk the inexperienced defender in the relegation battle that Swindon found themselves in - and before the end of March, he returned to Alfreton on loan, as Flint captained the Reds to the Conference North title, whilst Swindon were getting relegated to League Two. When Alfreton's season ended, Flint returned to the fray for the last game of the season - caretaker boss Paul Bodin giving him a five minute cameo at Tranmere, as the Town won 2-0.
Following Swindon's relegation, Scott Cuthbert, Lecsinel Jean-Francois and Andy Frampton all left the club, leaving Flint as the only recognised centre-back - new boss Paolo di Canio bringing in Joe Devera and Alberto Comazzi as competition, plus Oliver Risser and Alessandro Cibocchi who could also play in the position. Nonetheless, Flint started the season as first choice - and opened the campaign with his first goal in Town colours, scoring the Town's last goal with a headed effort in a 3-0 victory over Crewe, after a dominant display that won the man-of-the-match award.
Flint started each of the first eight games, as Swindon made a bad start to the season - before a hip injury forced him out at the beginning of September, and though the Town were facing somewhat of a defensive injury crisis, when he did return to full fitness, the Town's form had picked up - the partnership of makeshift defender Alan McCormack and Devera kept him out until the middle of October. A 3-3 draw with Hereford prompted di Canio to make changes, and Flint was paired with McCormack for the first time for the visit to Accrington Stanley - a partnership that became first choice for the remainder of the season. Flint added to his goalscoring tally with a headed equaliser against Huddersfield in the FA Cup in November which helped the Town to a 4-1 win, then in January, he opened the scoring in the Johnstone's Paint Trophy semi-final first leg at Barnet, which Swindon went on to win 2-1 on aggregate. Unfortunately for Flint, he was to miss the Wembley final - a groin injury picked up during training at the end of January initially reported to have ended his season prematurely - a second opinion from a specialist reducing the prognosis to six weeks.
As it was, Flint was out of the side for two months - and though he returned to the starting eleven for a 2-0 defeat at Crewe in mid-March, without full match fitness, he was dropped to the bench for the promotion clash with Torquay three days later, and didn't make the sixteen for the trip to the national stadium the following weekend. He returned to action for the visit of Bristol Rovers at the end of the month, and was ever-present for the remaining nine games of the season, Swindon clinching promotion to League One, and then the League Two title with a 5-0 victory over Port Vale, in which Flint netted the fourth goal.
Flint began the 2012/13 season behind new signing Troy Archibald-Henville in the pecking order, but was soon restored to the starting eleven when Archibald-Henville picked up a knee injury that would plague him throughout the season. After starting the league games against Crawley and MK Dons, Flint opened his goalscoring account for the season at Premier League Stoke, netting with a header that put the Town 3-2 up in extra time, in a game they would go on to win 4-3.
After the arrival of the experienced Darren Ward, Flint struck up a defensive partnership with the new man throughout September and October, until Flint was sent off in the first half of a game with Scunthorpe, picking up a second yellow card for tripping former Town striker Leon Clarke as he threatened to break past him and into the penalty area. Flint returned after just one game on the sidelines, but just three games later, he was again given his marching orders - this time a straight red card despite appearing to win the ball with a challenge on the halfway line in an FA Cup tie against Macclesfield. When the Town slumped to an embarrassing exit against their non-league opponents, boss di Canio singled out Flint for criticism - stating that he had already warned Flint about staying on his feet, and that the challenge was unnecessary - after sitting out a four game ban, Flint vowed to learn from his mistakes, but admitted that he felt aggrieved to have been sent off for a challenge that would have been deemed a good tackle a few years previously.
When Flint became available again, his place in the side had been taken by Joe Devera - and though he played in a 1-1 home draw with Doncaster at the beginning of December when Devera was moved out to left back to replace Jay McEveley, that proved to be the only game he played until mid-January, as the Town went through a purple patch of form from the middle of December and into the new year. When the transfer window opened, with interest from Plymouth, Port Vale and Bradford, di Canio stated that he might be tempted to part with Flint if it meant that he could use the funds to keep loan trio Danny Hollands, John Bostock and Chris Martin - but when Bradford made a formal approach, and Port Vale attempted to sign the defender on loan, both bids were rejected, and Flint returned to the starting eleven for a 2-0 win over Shrewsbury.
After coming on as a first half substitute for the injured Joe Devera at Leyton Orient in the following game, Flint kept his starting place for the rest of the season - a period in which di Canio left the club, with new boss Kevin MacDonald sticking with Flintís partnership with Ward at the heart of the defence. After the Townís push for automatic promotion fell away, Flintís second and third goals of the season helped the Town to a 3-0 win over Stevenage that secured a play-off place (a game in which he was unlucky not to score an unlikely hat-trick). Flint scored again in the play-offs - a crucial headed goal deep into injury time in the second leg of the semi-final, saving the Town from elimination right at the death - the goal causing pandemonium in the away end, as it pulled the tie with Brentford back to 4-4 on aggregate, and into extra time - Flint harshly booked for the celebrations. When the game went to a penalty shoot-out, Flint netted again - only for Brentford to score all of their efforts and book their place at Wembley.
The penalty proved to be Flintís last action in a Town shirt. At first, it seemed likely that Flint would stay at the County Ground, as the club activated a yearís extension to his deal, and rejected the advances of two clubs for his services. After Bristol City came back with an improved offer of £275,000 that was also rejected, Flint handed in a transfer request, only for that, as well as a third bid of £300,000 from Bristol City, to also be rebuffed. Eventually, a deal was done that would see the sell-on clause to former club Alfreton also covered by City, plus further incentives depending on appearances and performance, and after signing a four year deal at Ashton Gate, Flint thanked Swindon for giving him a start in the professional game, stating that he felt the move offered him his best chance of playing Championship football.
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