In 1992, Cunningham's work took him to Dooradoyle, Limerick, and he joined Garryowen, for whom his father had also played for, and was pressed into the first XV after Keith Wood suffered a shoulder injury. He remained in the team throughout the 1992–93 season and won the Munster Senior Cup against Limerick rivals and newly crowned All-Ireland League champions Young Munster. With Wood focusing on his Ireland commitments for the 1995 Rugby World Cup, Cunningham won a second Munster Senior Cup in 1994–95, and an injury to Terry Kingston saw him earn the first of eight caps for Munster in 1995.[citation needed]
His performances for Munster saw Cunningham earn selection for the Ireland A squad and a contract offer from the IRFU, but three months into the contract he suffered a popped disc which hampered his career. Despite playing in Munster's interprovincial games in 1996–97, he was then dropped, though continued to play for Garryowen.[1]
As well as rugby, Cunningham is also a qualified chartered accountant and financial analyst. He is also a rugby union coach, having been in charge of the Ireland Clubs team,[2] which selects from the amateur All-Ireland League, and, from 2013 to 2017, was head coach of Old Belvedere.[3]