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The first Headmaster was Ralph Herbert Dickinson born 1867, who served for 26 years. He was appointed on 1st September 1901, and was previously the Headmaster of the Wesleyan Day School in High St West. Mr Dickinson has been credited with establishing firm foundations for the new school, due to his enthusiasm and commitment. He retired on 31st December 1927. |
| Mr Dickinson was succeeded by Mr Charles Hartland Chambers, who was appointed on 1st January 1928, he had been the Senior Master since September 1903. He was a noted historian. He retired on 31st August 1937 after 34 years association with the school, including 9 years as Headmaster. |  |
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The 3rd Headmaster, Mr Cecil Lord, was appointed in September 1937. He was previously Head of English at Stretford Grammar School. He retired at the end of the Summer Term in 1960 after 23 years’ service.
For the Autumn Term of 1960, the Deputy Head, Mr Leonard E Hall, was acting Headmaster until the school Governors decided who was to be Mr Lord’s successor. |
| In January 1961, Mr John Climo was appointed the 4th and last Headmaster of Glossop Grammar School and in 1965, when Comprehensive Education was introduced in Glossop, he was appointed as 1st Headmaster of Glossop School. His 10 year service included 4 years as Head of the Grammar School and 6 years as Head of the Comprehensive School. |  |