Denny, Stirlingshire born inside forward Jimmy Dougal began his football career at Kilsyth Rangers in 1931, joining Falkirk in 1932. He soon made a significant impression and in January 1934 he was signed by Second Division Preston North End, helping them gain promotion as Second Division runners up at the end of the season. He was a member of Preston’s team beaten 3-1 by Sunderland at Wembley in the 1937 FA Cup Final but he missed their victorious 1938 Final win over Huddersfield Town having been injured in the semi final against Aston Villa. He top scored with 19 goals for Preston in 1938-39 and was selected to represent Scotland, scoring the Scotland goal in a 2–1 defeat against England in April 1939. He also scored in an unofficial wartime international, also against England, in May 1940. The Second World War denied him of a significant part of his career and he returned to Deepdale in its aftermath, although he only added one goal in 11 more games to his total of 57 goals in 202 appearances before joining Carlisle United in October 1946. In 2 years at Brunton Park he scored 14 goals in 74 games, before moving to Halifax Town in October 1948, playing 23 games, scoring twice, over the remainder of the season before joining non league Chorley in the summer of 1949.