Doncaster, Yorkshire born centre half Reg Hollingworth started his football career playing amateur football for Nuffield Colliery in 1925, Mansfield Town in 1926 and Sutton Junction in 1927. While playing for Sutton Junction he was spotted by First Division Wolverhampton Wanderers, and he joined the Second Division club on 8th November 1928, making his Football League debut two days later in a 2-0 win at Black Country rivals West Bromwich Albion. He made only sporadic appearances during his first seasons with the Molineux club, but became a first team regular from the start of the 1930-31 season, missing only one match that season as Wolves finished 4th in the Second Division.
The following season he was again a bedrock of their defence as the club won the Second Division Championship in 1932. He selected by England to play in a trial match in March, preceding a Home International against Scotland, but he was forced to pull out after damaging his ankle on the eve of the game in a League match, and he never won a cap for his country.
Injuries began to persistently restrict his career over the following years, and although he played most of their matches in the 1934-35 campaign, they eventually caused him to announce his football retirement at the end of the 1935-36 season, aged only 26. He had made 180 appearances in total for Wolves, scoring eight times in old gold and black.