Glossop is the smallest town to have been represented in the top flight of English football. In 1900, when the Hillmen were plying their trade in the top division, the population of Glossop numbered roughly 21,000. They may have only lasted a single season in Division One, but before World War One Glossop were one of the most recognisable names in English football. Glossop's season in the top flight was only their second in the Football League. In their first, they had finished 2nd in the Second Division. After relegation, they spent their remaining years as a middling side in the Second Division, with a Quarter Final finish in the FA Cup being the Hillmen's greatest success post 1900. In the last season of prewar football, Glossop finished bottom of Division Two. After five years of war, Glossop were finally able to reapply for the Football League, an application which was rejected. After the failure of the Hillmen to rejoin the Football League in 1919, they joined non-league football, where they remain today as Glossop North End.