Macclesfield's Historic FA Cup Upset Against Crystal Palace
Macclesfield Town, a sixth-tier club, may have achieved the greatest upset in the FA Cup's 155-year history.
On Saturday, the National League North team triumphed over the reigning FA Cup champions, Crystal Palace, with a score of 2-1, despite being ranked 117 league places below the Premier League side. This remarkable victory stands as the most significant upset in the tournament's history based on the disparity in league rankings.
But how does this victory rank among the most surprising moments in the history of football's oldest cup competition? We have compiled a list of ten of the biggest upsets for you to consider and rank. Feel free to share your thoughts in the comments.
Match Summary: Macclesfield 2-1 Crystal Palace (Third Round, 2026)
Despite their lower league status, Macclesfield earned their victory with a performance that fully justified their win. Paul Dawson's brilliant header in the first half sent the home crowd into a frenzy, followed by Isaac Buckley-Ricketts scoring a second goal shortly after the break.
Yeremy Pino's late free-kick goal in stoppage time created a tense finish for the hosts, but Macclesfield held on for the win. Crystal Palace arrived in Cheshire with an injury-plagued squad and were winless in eight matches, a stark contrast to their FA Cup success less than eight months prior, when they defeated Manchester City in the final.
This victory is particularly poignant for Macclesfield, a club that only resumed play in the 2021-22 season after the original Macclesfield Town was liquidated in 2020 due to significant debts. The day was especially emotional for players, staff, and fans as they mourned the loss of forward Ethan McLeod, who tragically died in a car accident on December 16 while returning from a match.
Historical Upsets in the FA Cup
Throughout the years, the FA Cup has witnessed numerous stunning upsets. Here are some notable examples:
Bournemouth 2-0 Manchester United (Third Round, 1984)
Facing FA Cup holders Manchester United, Bournemouth, then struggling in the Third Division, shocked everyone by securing a 2-0 victory. Under the management of Harry Redknapp, the Cherries matched United for an hour before scoring two quick goals.
Stevenage 3-1 Newcastle (Third Round, 2011)
In their first season of league football, League Two's Stevenage defeated Premier League Newcastle with a dominant performance, marking one of the biggest upsets in recent FA Cup history.
Shrewsbury 2-1 Everton (Third Round, 2003)
Managed by Everton's former captain Kevin Ratcliffe, Shrewsbury stunned their higher-placed opponents, with captain Nigel Jemson scoring twice to secure a historic win.
Plymouth 1-0 Liverpool (Fourth Round, 2025)
After making ten changes to their squad, Liverpool fell to Championship side Plymouth, who took advantage of a penalty to secure a remarkable victory.
Chelsea 2-4 Bradford City (Fourth Round, 2015)
In a thrilling match at Stamford Bridge, Bradford City overturned a two-goal deficit to claim a stunning 4-2 victory against Premier League Chelsea.
Oldham 3-2 Liverpool (Fourth Round, 2013)
League One Oldham shocked Liverpool with a spirited performance, overcoming a strong Reds side to secure a memorable win.
Wrexham 2-1 Arsenal (Third Round, 1992)
Wrexham, bottom of the Fourth Division, pulled off a stunning upset against First Division champions Arsenal, scoring two late goals to snatch victory.
Sutton 2-1 Coventry (Third Round, 1989)
Sutton United, a non-league team, upset Coventry City, then a First Division side, with a memorable home victory.