Woolston, Southampton born outside left Jack Roy played for Sholing Athletic in 1932 before joining Third Division (South) club Norwich City in July 1933 on amateur forms, turning professional the following month, for whom he made his debut against Gillingham in January 1934 in a Third Division Cup match. His Football League debut wasn’t until September, when he played at Newcastle United in a Second Division match after Norwich had been promoted as Third Division (South) Champions. But in three seasons in East Anglia he remained a fringe player, scoring once in 10 appearances.
He joined Mansfield Town on a free transfer in April 1936, and scored twice in 28 appearances for The Stags during 1936-37, his excellent form attracting First Division Sheffield Wednesday who signed him for £1,750 in February 1937, a record fee for Mansfield. Although he couldn’t help save them from relegation at the end of the season, he scored once in 16 games for The Owls before being signed by Notts County in March 1938. He played 16 games for The Magpies including 5 alongside their celebrated signing from Everton, the legendary but ageing Dixie Dean, before joining Tranmere Rovers the same December, scoring twice in 21 appearances for Rovers before joining Southern League club Yeovil & Petters United the following May.
He then lost six years to the Second World War, during which he played wartime football for Yeovil, Southampton, Aberaman Athletic and Ipswich Town. He was one of the few players to be transferred during the War, signing for Southampton on Christmas Day 1939.
But after the conflict he returned to East Anglia and to Football League action, joining Third Division (South) Ipswich Town in February 1946, scoring twice in 17 appearances during the first peacetime League season of 1946-47 before transferring to non league Gravesend & Northfleet in October 1947, finally re-joining the (by now re-named) Yeovil Town in 1948, subsequently playing for Somerset club Chard Town before his eventual retirement.