Ryan initially played Gaelic football for the Marino School in Dublin whilst growing up but discovered soccer after moving to Blackpool early in the Second World War. He was a natural sportsman and after trials with several league clubs he joined Nuneaton Borough. Whilst there Harry Storer selected him as an amateur guest for City on six occasions.  In April 1945 Ryan signed for West Brom and commenced a successful ten-year career with the Baggies. The skilful wing-half/inside forward helped Albion to promotion to Division 1 in 1949 and was a member of the 1954 team that won the FA Cup and were pipped for the league championship. In all Reg made 272 appearances in Albion’s colours and whilst at the Hawthorns won 16 caps for the Republic of Ireland and one cap for Northern Ireland under strange qualification rules at the time.

After leaving Albion in 1955 former City boss Harry Storer now manager of Derby County signed him and he skippered the Rams to promotion from Division Two. In 1958 Billy Frith signed him for Coventry and he was an inspirational skipper as City won promotion from Division Four at the first attempt. He arrived at Highfield Road when City were struggling in the lower reaches of the bottom division but his experience and ability together with a never say die attitude rubbed off on the team. Reg hung up his boots in 1960 at the age of 35 and helped manage the clubs’ pools scheme for a year. Later he moved back to West Brom as chief scout – a role he fulfilled for 14 years and he continued scouting for various clubs until his retirement in 1994.