Age: 37 years, 6 months
Place of Birth: Strabane, Northern Ireland
Nationality: Northern Ireland
Height: 5' 9"
Rory began his career with Rochdale in England where, after a period as a trainee, he signed his first professional contract in the summer of 2002. He made his league debut against Oxford United in November 2002. Over the next two seasons Rory made 15 league appearances for the club but in the summer of 2004 he was released, despite winning Rochdale's Young Player of the Year award for 03/04.
He had short spells at Radcliffe Borough and Mossley before settling at FC United of Manchester in 2005. He made 126 appearances and scored 107 goals over the following three seasons but moved on to sign for Bradford Park Avenue in July 2008. In 2009 Rory had a brief spell at Droylesden but left the club on 27 June 2009 and returned to Northern Ireland where he signed for Coleraine. He made 33 league appearances and scored 30 league goals, adding a further 11 strikes in Cup competition.
In June 2010 Rory signed for Plymouth Argyle and scored four times in 35 league appearances over the next year. In July 2011 he went on loan to Irish League club Linfield where he scored four times in 18 league appearances and in January 2012, after some confusion over his contractual status, he signed for Declan Devine at Derry City.
Rory promptly scored a hat-trick on his debut for Derry, in a 4-0 win over Lisburn Distillery in a Setanta Cup game on 4 February 2012 and he made his league bow in a 1-0 home win over Bohemians on 2 March. He went on to bag five goals in 13 league appearances despite having his season interrupted by injury and he also scored twice in the FAI Cup final as Derry beat St Pats 3-2 in the final at the Aviva. In his second season at the Brandywell he scored 25 goals in league and cup as Derry finished fourth in the Premier Division.
Rory stayed with Derry City for the 2014 season and went on to score eleven goals in 23 league appearances as Derry finished eighth in the Premier Division table. He also scored four goals in four games in Derry's European run, including a hat-trick in the 5-0 win in the away leg against Aberystwyth and another in a 4-0 win against the same side in the home leg. He also played in the FAI Cup Final, which Derry lost 2-0 to St Pats.
In January 2015 Rory agreed to cancel his contract at Derry City due to the financial difficulties that the club were in. He firstly signed for Australian side Cockburn City in February 2015, where he made 19 league appearances and scored twenty goals, twice netting four in a game, as they finished fifth in the National Premier League in Western Australia. After the season's end, in October 2015, Rory returned for a second spell at FC United of Manchester. He went on to make 5 substitute league appearances and came off the bench in the 4-1 loss to Chesterfield in the FA Cup. He also started in the 4-3 loss to Staylebridge Celtic in the Manchester Premier Cup whilst and was sent off after coming off the bench in the 2-1 loss to Telford Athletic in the FA Trophy.
In December 2015, Rory returned to Foyleside to sign for Kenny Shiels at Derry City. He missed just one league game in 2016, scoring 17 league goals in 32 league appearances, adding three more goals in Derry's run to the FAI Cup semi-finals. Rory re-signed with Derry City for the 2018 season.
In January 2021, Rory signed for Dungannon Swifts.