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On 15 January 2018, Flynn joined St Mirren on a two-and-a-half-year deal. Flynn suffered cruciate ligament damage on 5 February 2020 in a match against Hamilton Academicals, which effectively ended his season.

On 13 July 2016, Flynn signed a two-year deal with League One side Oldham Athletic. He scored his first goal for Oldham in a 2–1 EFL Cup win against Wigan Athletic on 9 August 2016. He was released by Oldham in January 2018.

In May 2014, Flynn signed an extension to his contract for a further two-year with the option of a third year.

In 2014–15 Flynn and Sheffield United went on another famous cup run, this time making the semi-final of the League Cup. They beat West Ham at Upton Park as well as Southampton at Bramall Lane en route to the Semi Final where they met Spurs and lost narrowly 3–2 on aggregate. Flynn showed his versatility by starting both games against Spurs at right back and performing impressively. The season ended once more with United making the League One Play Offs only to lose to Swindon Town 7–6 on aggregate.

In season 2012–13 Flynn appeared 44 times for the Blades scoring three goals as the side again made the play offs in League One. In 2013–14 Sheffield United embarked on a memorable FA Cup campaign which culminated in them reaching the Semi-Final at Wembley in which they lost 5–3 to Hull City. Flynn starred for the side throughout the campaign, scoring the winning goal against Premier League side Aston Villa at Villa Park and also scoring as they beat Championship side Charlton.

On 14 July 2011, Flynn signed for Sheffield United for an undisclosed fee on a three-year deal and made his competitive club début on the first day of the 2011–12 season, starting the Football League match against Oldham Athletic. During his first season at Bramall Lane Flynn established himself as first team player despite competing with the likes of Republic of Ireland International Stephen Quinn for a place in the starting eleven. He finished the campaign having made thirty five appearances and scored three goals. This campaign ended with United finishing 3rd in League One and making the Play Off final. Flynn started in this game as United lost on penalties to Huddersfield at Wembley.

Flynn was then loaned back to his first club, Falkirk, for the 2009–10 season. He made his Falkirk début in a UEFA Europa League tie against FC Vaduz, and Flynn scored the only goal of the game, becoming the first Falkirk player to score a goal in European competition. In mid September it was announced that his move had been made permanent and he signed a three-year contract with Falkirk. Flynn won the Scottish Premier League award for Young Player of the Month for March 2010, having scored six goals in 33 games for Falkirk. He also won the Young Player of the Round award in the second round of the 2010–11 Scottish League Cup, in which he scored the only goal to put Falkirk through against Partick Thistle In the third round of the same cup he was part of the Falkirk team that were voted 'Team of the round', a game in which he scored the third goal against Hearts and which ended up 4–3 to Falkirk.

Flynn began his career as a junior player with Falkirk, but signed for Liverpool in 2005 for £50,000. Flynn helped Liverpool win successive FA Youth Cup victories in the 2005–06 and 2006–07 seasons, scoring the winner in front of the Kop against Manchester City in the 2006 final and scoring in the penalty shoot-out at Old Trafford (Stretford End) against Manchester United in the 2007 final. In his third season at the club, he helped them win the Northern Premier Reserve League Title, in the 2007–08 season. Flynn was loaned to Conference National club Wrexham for the latter part of the 2008–09 season,. In all, Flynn scored four goals in 25 league appearances for Wrexham.

Ryan Flynn (born 4 September 1988) is a Scottish footballer, who plays as a midfielder for St Mirren. Born in Edinburgh, he started his career with Liverpool before spells at Wrexham, Falkirk, Sheffield United and Oldham Athletic. He has also represented Scotland at under-19 level.