Stapleford, Nottinghamshire born winger Dennis Watkin began his football career with Stapleford in 1927 from where he joined First Division Aston Villa, making his Football League debut at Leeds United in December 1932. He scored 4 goals in 11 appearances in 1934-35 for Villa but he was released in the summer of 1936 after their relegation, having scored 5 goals in 21 appearances. He joined Reading for whom he was the club’s top scorer in 1936-37 with 17 goals in the campaign, and for whom he played until 1939, scoring 27 goals in 96 appearances, but his career was effectively ended by the outbreak of the Second World War in September 1939.
He was also a first class cricketer who played for 9 matches for Nottinghamshire between 1937 and 1939. Bowling leg-breaks, Watkin bowled 200 overs and took 15 wickets at just under 50 a piece, with a best performance of 6-48, his only 5 wicket innings. As a batsman, he was a tail ender, with a high score of 14 and an average of just less than 6 in 12 innings.