Glossop North End were founded in 1886, when they played friendly amateur matches. They played at a variety of grounds, including Pyegrove, Silk Street, Water Lane and Cemetery Road before settling at North Road.
The club joined the North Cheshire League in 1890, before moving to The Combination in 1894 and becoming a professional club. In their first season, 1894-95, in the Combination they were runners-up. After finishing third the following season, the club moved to the Midland League in the 1896-97 season, finishing as runners-up. After a second season in the league, they were elected to the Second Division of the Football League in 1898–99 finishing as runners-up and winning promotion to the First Division. They then changed their name to Glossop before spending their one and only season in the top flight, 1899–00 when they finished in last place and were relegated back to the Second Division. They then spent the next fifteen seasons in the Second Division, during which time they reached the quarter-finals of the FA Cup in 1908–09 where they lost to 1-0 to Bristol City in a replay on 10 March 1909. The club's chairman and benefactor at the time was Sir Samuel Hill-Wood, who was later to become chairman of Arsenal. However, the club struggled for several seasons in the Second Division.
The 1913–14 season saw a club record attendance of 10,736 for an FA Cup second round match against Preston North End on 31 January 1914. However, the following season they finished bottom of the league and they failed to be re-elected. The start of World War I meant the Football League closed down. Glossop were re-formed toward the end of the war by Oswald Partington. Glossop then joined the Lancashire Combination, playing just one season, 1919-20. Northern Nomads ground-shared with Glossop for several years during this time. The club then dropped out of the Lancashire Combination and into the Manchester League. In the 1920s and 1930s they won the Gilgryst Cup three times and were crowned Manchester League champions in 1927-28. They won the Gilgryst Cup for a fourth time in 1947-48.
In 1957 Glossop rejoined the Lancashire Combination, finishing in eighth in 1957-58. They spent nine seasons in the league before dropping back down once more to the Manchester League after the 1965-66 season. They joined the Cheshire County League as founder members of Division Two in the 1978-79 season, finishing in 17th. In 1980-81 they were Division Two runners-up, only losing out on the title on goal difference, but still winning promotion to Division One. After a sixth place finish in 1981-82, the club became founder members of the North West Counties Football League in 1982 when the Cheshire County League merged with the Lancashire Combination. In 1986, the club marked their centenary with a match with Arsenal. They joined Division One, however they struggled in the league for the next six seasons and after finishing bottom in 1987-88 were relegated to Division Two. The 1990-91 season saw the club reach the fourth round of the FA Vase where they lost to Cammell Laird 2-1 in a replay. They also won the North West Counties Football League Division Two Cup, beating Cheadle Town 2-1 in the final. However, the club almost folded in 1990-91 when their then Chairman sold the ground to the local council and left the club with large debts. The present Board of Directors took over in January 1991. After a sixth place finish in 1991-92 they were promoted back to Division One over higher-placed clubs and after the season the directors reverted the club's name back to Glossop North End.
In their first season under the club's original name, 1992-93 they finished 16th in Division One. In the 1992-93 season, they reached the semi-finals of the North West Counties League Cup, before losing to Nantwich Town 5-2 over two legs. They reached the semi-finals of the league's Floodlit Cup in 1994-95 losing to Penrith 3-1 over two legs. In the 1996-97 season they beat Trafford in the final of the Manchester Premier Cup at Old Trafford, before winning the competition again the following season, this time beating Radcliffe Borough in the final at Maine Road. They also reached the semi-finals of the North West Counties League Cup losing to Vauxhall Motors 3-1 over two legs. The 1999-2000 season saw the club reach the fourth round of the FA Vase where they lost to Chippenham Town 1-0.
In the 2000-01 season they won the Derbyshire County Football Association Senior Challenge Cup beating Glapwell in a two-legged final, drawing 3-3 away and 2-2 at home before winning 4-2 on penalties. In the league the club struggled to avoid relegation from Division One throughout much of the early 2000s, before finishing ninth in 2006-07, the highest position attained by manager Chris Nicholson in his six seasons at the club. The highlight of the season was a four match FA Cup run. In the extra preliminary round they beat North Shields 2-0, then after a 2-1 home win over Seaham Red Star they were drawn against local rivals New Mills in the first qualifying round, a match which Glossop led 1-0 at half time, only for the Millers to equalise with ten minutes to go. Glossop then quickly regained the lead, before adding a third to win 3-1 in front of a season highest crowd of 430.
Nicholson had announced in March 2007 that he was to step down at the end of the season following confirmation of his emigration to Perth, Australia. As a result the vacancy was advertised and his assistant Steve Young was eventually appointed manager for 2007-08. In 2007-08 North End made excellent strides on the pitch, finishing in seventh, which might have been fifth but for a last game defeat at the hands of champions Trafford. It took a while for the team to gel, which led to early cup exits at Malvern Town in the FA Cup and Coventry Sphinx in the FA Vase. However, they hit their stride in early November, including a run of wins that propelled them up the league. Darren Hamilton who scored 21 goals during the season, and who had been at the club for ten years, won the Supporters Player of the year award.
In the 2008–09 season they reached the final of the FA Vase where they lost 2–0 to Northern League First Division side Whitley Bay at Wembley Stadium, on May 10, 2009. Due to this achievement, Arsenal, with whom they retain connections due to Arsenal chairman Peter Hill-Wood's grandfather Sir Samuel Hill-Wood having owned and bankrolled Glossop during their run in the Football League, invited them to their state-of-the-art London Colney training ground during their stay in London, to prepare for the FA Vase final.