Manager Sammy McIlroy led Macclesfield Town to the top of the Conference in 1993–94, but they were not promoted as Moss Rose did not meet Football League requirements.

After a points deduction activated on 11 August 2020, the club was relegated to the National League, the 5th tier of English football, for the 2020–21 season.

It was agreed at a public meeting on 21 October 1876 that the 8th Cheshire Rifle Volunteers and the Olympic Cricket club teams be merged to form Macclesfield F.C.

Macclesfield became members of The Combination at the start of the 1890–91 season and moved from Victoria Road to the Moss Rose on 12 September 1891 which remains the home of the Silkmen today.

From a high of a fourth place league finish in 1989–90, Macclesfield Town's final standing diminished each season, and following a struggle against relegation in 1992–93, manager Peter Wragg was sacked, and replaced with former Manchester United midfielder Sammy McIlroy.

[8] Macclesfield Town won the Conference title again two seasons later in 1996–97, by which time the stadium had been upgraded and they were promoted to Division Three of the Football League in place of Hereford United.

David Moss in turn succeeded Prescott as manager and delivered two decent mid-table finishes, but a bad start to the 2003–04 season resulted in his sacking.

Club stalwart John Askey succeeded Moss initially on a temporary basis, and earned the job permanently with some promising early results.

Horton reinvigorated Macclesfield Town who finished fifth in the 2004–05 season, resulting in a playoff place, but the team were eliminated in the semi-finals by Lincoln City.

They were then just able to survive after drawing 1–1 with Notts County on the final day of the 2006–07 season, after a poor run of results landed the team back in the relegation zone; this game also saw the last appearance (and booking) of Paul Ince as a professional footballer.

He was replaced by club supporter Mike Rance, with ex-player Andy Scott, founder of Bank Fashion Retail stores, as vice-chairman.

[16] Macclesfield Town failed to win any match from the start of January 2012 until the end of the season (23 league and two FA Cup games; eight draws and 17 defeats).

[17] After defeat at Dagenham & Redbridge on 17 March continued a winless streak of 14 League matches, Simpson was asked to step down as manager by chairman Mike Rance, and was replaced by Brian Horton.

However, Horton was unable to change Town's poor form and the team were relegated to the Conference Premier on 28 April 2012 following a home defeat to Burton Albion.

Horton then left the club and Glyn Chamberlain took charge of the team for the final game of the season, before Steve King was appointed as manager on 21 May 2012.

[24] After Danny Whitaker and Neil Howarth briefly took temporary charge, former Premier League and England defender Sol Campbell was appointed manager in November 2018.

Six players issued a winding-up order against the club, which was taken over by HM Revenue and Customs in September but the High Court hearing was adjourned 10 times.

[38] A strike by first team players over the unpaid wages jeopardised Macclesfield's FA Cup first round tie against non-league Kingstonian at the Moss Rose on 10 November 2019,[39] but the club fulfilled the fixture, fielding six youth team players and five loanees,[40] losing the tie 4–0 amid protests from Macclesfield supporters, many of whom boycotted the game.

[46] Two weeks later, Macclesfield players again told the club's owner they would not train, or play on 7 December against Crewe Alexandra, if owed wages were not paid.

[32] Frustrated by the club's financial position, with December's pay arriving late, manager McMahon resigned after four months in charge, on 2 January 2020,[56] joining Dagenham & Redbridge the following day,[57] along with assistant Steve Gritt.

[60] On 29 January, three Macclesfield players (Emmanuel Osadebe, Theo Vassell and Miles Welch-Hayes)[61] approached the EFL and had their contracts terminated ahead of the transfer deadline.

[74] In the meantime, the club provided the EFL with a "robust" business plan showing sustainable future financial and management resources,[75][76] and on 4 August, chairman Amar Alkadhi resigned his position.

[79] On 9 September 2020, the High Court granted Macclesfield a seven-day extension (effectively a 12th adjournment) to a winding-up petition over unpaid tax to give time for a possible takeover of the club by Robert Benwell (previously linked with a move to buy Bury F.C.).

[81] However, on 29 September 2020, the club was suspended by the National League and its first three scheduled games were postponed, pending a notice of expulsion taking effect from 12 October 2020.

However, many loyal supporters were not happy with the modern design so the plans were delayed and a re-designed badge was introduced in early 2008, which won the approval of the majority of fans.

Before moving to the Moss Rose, three other grounds were used: Macclesfield Grammar School, Rostron's Field (near Coare Street) and Victoria Road (then known as Bowfield Lane).

[88] Phythian's Saga of the Silkmen (p. 85) and the News of the World Football Annual both give the record attendance of Moss Rose games involving Macclesfield Town as 9,003, in the Cheshire Cup tie vs. Winsford United, 14 February 1948.

In September 2007, the club made a statement about possibly relocating to a new stadium in the proposed 'South Macclesfield Development Area', approximately one mile south of the Moss Rose.

Most supporters are from Macclesfield and its environs with small pockets of fans from Norway, Japan,[92] Port Talbot in south Wales and Fleet in Hampshire (The Southern Silkmen Lads – SSL).

On 23 April 2021, local band and Macclesfield fans, Glass Ankle released a video for their song "Super Silkmen" which featured clips recorded by supporters whilst in COVID lockdown, as well as photos of former players and managers held in high esteem.