Diminutive of stature, Esh Winning, County Durham born winger Monty Wilkinson began his football career with Esh Winning and Kelloe Colliery in 1923. After an unsuccessful trial at Sunderland he returned to Esh Winning before spending 1925-26 on the books of Durham City without making their first eleven. In 1926 he joined Crook Town, where he scored 100 goals in a single season and attracted the attention of First Division Champions Newcastle United, who signed him in May 1927 for £250, his Football League debut coming at Aston Villa that October. He scored a hat-trick in the return fixture with Aston Villa in March 1928 although he struggled for first team opportunities at St James’ Park and joined Everton for £675 in June 1929 after 11 goals in 27 appearances.
He played only sporadically for Everton, making six appearances as they were relegated in 1930, and scoring twice in 6 appearances as they were immediately promoted as Second Division Champions in 1931, but he joined First Division Blackpool in March 1931. He had two seasons at Bloomfield Road but when they were relegated in 1933 he left to join Second Division Charlton Athletic in February 19333 after 15 goals in 63 appearances for The Seasiders, but he couldn’t help save them from relegation to the Third Division (South) by the season end. It is for his deeds at Charlton that he is perhaps best remembered.
He was a near ever present in his first season at The Valley, second top scoring with 12 goals as The Addicks finished fifth, and then scoring 13 goals in the campaign as they won the Third Division (South) Championship in 1934-35, missing only four games. He then missed three games as they won promotion from the Second Division as runners up in 1935-36. He remained a fixture in Charlton’s first eleven as they finished runners up in the League Championship itself in 1936-37, followed by fourth and third place finishes in the final two seasons before the Second World War, which effectively ended his career after 51 goals in 238 appearances for The Addicks. During the War he served with the RAF in Burma.