New Brighton, Cheshire born left back Reg Freeman began his football career was an accomplished full back who began his football career with Wallasey Rovers in 1912, playing for Harrowby in 1913 and Yorkshire Amateurs in 1914 before the onset of the First World War. He had played for Liverpool in wartime football and played for Northern Nomads in 1919, but started his Football League career with First Division Oldham Athletic after the War, making his Football League debut against Bolton Wanderers in January 1921. He was an ever present in The Latics’ 1921-22 campaign and missed only three games as they were relegated the following season.
He signed for Middlesbrough for £3,600 in May 1923 after 104 games for The Latics. At ‘Boro he played seven seasons, winning the Second Division Championship in 1927 and 1929 (he was injured for most of their 1927-28 relegation season) and being Club Captain, making 187 appearances before joining Rotherham United for £150 initially as a player in 1930.
He went on to play 98 games for Rotherham scoring his only 3 career goals for them, he then served The Millers for 18 years as manager from January 1934 to 1952, winning the Third Division (North) Championship in 1951. In 1952 he became manager at Sheffield United and led them to the Second Division title in 1953, keeping them in the First Division over the next two seasons, however he died aged 61 before the start of the 1955-56 season.