If van Persie had hit the kind of goal he got in the derby then we would all have been raving about it. It was such a good strike and it showed what Ryan has to offer when he is in that kind of form. He just needs to believe in himself more and once he has that confidence he can do even greater things. Not many people have the sort of left foot he has. Ryan can make things happens and I have asked him to do that." During the 2012–13 season, he made thirty-eight appearances in all competitions, scoring seven times, making him Dundee's top scorer for the season, however, the club was relegated after a draw with Aberdeen. Ahead of the 2013–14 season, Conroy signed a new deal with the club. He scored seven goals as Dundee won promotion to the Scottish Premiership by winning the 2013–14 Scottish Championship, but he was released by the club in June 2014, having been among players expected to leave in the summer. Raith Rovers On 10 July 2014, Conroy signed with Raith Rovers. At the time of his release from Dundee, Raith Rovers confirmed their interest in signing Conroy. He scored on his debut, against Forfar Athletic on 2 August 2014, in a 4–2 win in the Scottish Challenge Cup. His first league goal came seven days later on 9 August 2014, in the opening game of the season, in a 3–1 win over Dumbarton, followed up his second goal, in a 1–0 win over Alloa Athletic in his second appearance. Following his good display, Manager Grant Murray believed Conroy could be a key player for the club. Queen of the South (Second spell) On 28 May 2015 it was announced that Conroy had signed for Queen of the South. He scored on his second debut for the club against Stranraer in the Challenge Cup, and followed that up with another goal on his second appearance against Annan Athletic in the Scottish League Cup. Airdrieonians Conroy joined Scottish League One side Airdrieonians in July 2016, signing a two-year deal with the club. At the end of the 2018–19 season, he was among a group of players made available for transfer by the club, and on 3 July 2019, he left Airdrieonians after agreeing a mutual termination of his contract. Following his departure, Conroy criticised the club for making the list