Glossop North End were founded in 1886, when they played friendly amateur matches. They played at various grounds in the town, including Pyegrove, Silk Street, Water Lane and CemeteryRoad before settling at North Road. The club joined the North Cheshire League in 1890, before moving to the Combination in 1894 and turning professional. In their first season in the Combination, 1894/95, they finished as runners-up. After ending the following season, 1895/96, in third, the club moved to the Midland League and in the 1896/97 season finished as runners-up.
After a second season in the Midland League, they were elected to the Second Division of the Football League in 1898/99 finishing as runners-up to Manchester City and winning promotion to the First Division. They then changed their name to Glossop (primarily to avoid any confusion with Preston North End) before spending their one and only season in the top flight, 1899/1900 when they finished in last place and were relegated back to the Second Division, having won only 4 matches, all at home, against Burnley, Nottingham Forest, Blackburn and Aston Villa.
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 eventual finalists 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 became perennial strugglers 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 had to apply for re-election. This was curtailed when the start of World War I meant the Football League closed down. Glossop were then re-formed toward the end of the war by Oswald Partington but failed to be re-elected back into to the Football League. 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 Gilcryst Cup three times and were crowned Manchester League champions in 1927/28. They won the Gilcryst Cup for a fourth time in 1947/48.
During 1955, the club moved from its original home of North Road to their current ground Surrey Street. In 1957 Glossop re-joined 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 newly formed North West Counties Football League in 1982 when the Cheshire County League merged with the Lancashire Combination. In 1986, the club marked their centenary season with a match with sister club 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 to Glossop North End.
In their first season under the club's original name, 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.
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. Nicholson announced in March 2007 that he was to step down at the end of the season. As a result, his assistant Steve Young was eventually appointed manager for 2007/08. 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 10 May 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.
In May 2013 the club appointed Chris Wilcock as first team manager. In his first season the team finished third in the North West Counties League. During the season Glossop produced an unbeaten run in the league of 22 games, with only 5 draws, stretching from November 2013 until they were beaten by Bootle on April 2014.
On 19 April 2015 Glossop beat Nelson to win the North West Counties League Premier Division, earning promotion to Division One North of the Northern Premier League. They also reached two cup finals; the North West Counties League Cup, where they faced Atherton Collieries winning 2–0, and the FA Vase Final, in which they played North Shields at Wembley Stadium. In a repeat of the 2009 final, Glossop were beaten 2–1 after extra-time.
Glossop began the 2015/16 season in the Northern Premier League Division One North. They also competed in the FA Trophy for the first time since 1986. The club finished fourth and qualified for the Play-offs but lost 2–1 to Northwich Victoria in the Semi-Final.
At the end of the 2016/17 season Chris Wilcock resigned as manager, leaving the position after four seasons and as the winningest manager in recorded history. On 19 May 2017 the club announced that the joint team of Steve Halford and Paul Phillips would take the reins at Surrey Street. On 12 March 2018 the management team left Glossop to join Buxton. Goalkeeper coach Mark Canning took over as caretaker manager, assisted by Andy Bishop. This was made a permanent position at the end of the 2017/18 season. After a poor run of results, culminating in a loss to Widnes in mid-October, Mark and Andy were sack as managers. After a short search the board appointed ex-Mossley due Peter Band and Lloyd Morrison as joint managers on 14 October 2018 as the club went on to finish in 17th place in the table.