Clydebank, Dunbartonshire born outside right Jock Stirling began his football career with Clydebank Juniors before joining Scottish League club Clyde in 1908, from where he was signed by First Division club Middlesbrough in the summer of 1911, making his Football League debut at Sunderland at the start of September. He spent three seasons with the Ayresome Park club under the management of Thomas McIntosh and was a regular in the side which finished in third in the League Championship during the 1913-14 season, when he missed only 4 matches. After 9 goals in 112 appearances Stirling left Middlesbrough for Bradford Park Avenue in August 1914 where he spent the 1914-15 season before peacetime football was suspended due to the onset of the First World War, having scored twice in 34 appearances.
After the War, Stirling joined Second Division Stoke in 1919 for the first peacetime season after the conflict, scoring once in 21 appearances for The Potters as they finished mid-table. He then joined Coventry City in March 1920, and played 5 matches as Coventry narrowly avoided relegation. He then returned to Scotland in the 1920 close season, joining Alloa Athletic, and helped them to win the Second Division Championship in 1921-22 and their first promotion to the Scottish top flight before his eventual retirement.