 He scored his first goal for the club in a 2–2 draw with Cork City in the 2009–10 Setanta Sports Cup, Sligo's first ever goal in the competition.He struggled to get a regular place in the side for his first year and a half as he struggled with fitness but came into his own with a string of highly impressive passing displays in the successful 2010 season.Ryan was Player of the Month in October and won the 2010 PFAI Player of the Year award.