Unstone, Dronfield, Derbyshire born goalkeeper Harry Maskrey began his football career with Ripley Athletic in 1901, before being signed by First Division Derby County in December 1902, making his Football League debut in April 1903 against Grimsby Town. Initially understudy to Jack Fryer, he took over the goalkeeper’s gloves in November 1903, Fryer having moved to Fulham. In March 1904 he was in goal for Derby’s narrow FA Cup semi final defeat to Bolton by 1 goal to nil at Molineux, and in February 1906 he was rewarded for his consistency when he played for England against Ireland at Cliftonville’s Solitude Ground in Belfast in a 3-1 victory for England. He also played once for The Football League in a 4-0 win against The Irish League in October 1905.
Derby were relegated in 1907 but Maskrey remained in goal for them until First Division Bradford City signed him in October 1909 after 218 appearances for The Rams. At Valley Parade he dominated the gloves in his first season but lost out to Mark Mellors in December 1910, and Mellors would keep goal in Bradford’s 1911 FA Cup triumph. After 43 appearances for The Bantams Maskrey re-joined Ripley Town & Athletic in 1911 and moved to Stalybridge Celtic later the same year, before a move to Mansfield Mechanics in 1913 who became Mansfield Town a year later. With the First World War he served in the Grenadier Guards, and after the War he joined Celanese in 1919 before re-joining Derby County in 1920, making a further 5 League appearances for The Rams between September and December 1920. He then joined non league Burton All Saints in 1921.