The FA Cup, renowned for its surprises, witnessed its most astounding upset in 154 years on Saturday.
Non-league Macclesfield FC shocked the reigning champions, Crystal Palace, with a remarkable 2-1 win. The staggering 117 positions that separated the two teams in the football hierarchy marks this as the greatest upset the tournament has ever seen.
The match had the essence of a classic cup showdown, particularly when Macclesfield’s captain, Paul Dawson, netted the first goal. Moments before a deep free-kick, a teammate quickly bandaged his head, and Dawson decisively struck the ball into the net.
The game grew more thrilling as striker Isaac Buckley-Ricketts extended Macclesfield’s advantage after the hour mark, before Palace winger Yéremy Pino converted a free-kick deep into added time.
Macclesfield, who play in the sixth tier, managed to hold on and etch their name into FA Cup history. But how astonished should we be?
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Macclesfield became the inaugural team to win an FA Cup match against an opponent positioned five levels above them in the league. Additionally, they are the first non-league side to eliminate the reigning champions from the cup in 117 years, the last being… Crystal Palace against Wolves in 1909.
The only upset comparable in shock value is Sutton United’s legendary win over Coventry City in 1989. However, Macclesfield is currently a division lower than Sutton was at that time.
Ranking the Biggest Upsets in FA Cup History
1. Macclesfield 2-1 Crystal Palace
This stands out as the most significant upset ever recorded. No team at such a low level in the English football hierarchy has managed to eliminate a top-flight team, especially against the tournament’s reigning champions.
Moreover, there’s a notable twist: Manchester United legend Wayne Rooney’s brother, John, serves as Macclesfield’s head coach.
“I feel emotional witnessing my younger brother achieve this,” Rooney shared with the BBC. “He’s relatively new to management; reaching the fourth round of the FA Cup and defeating a Premier League team like Crystal Palace fills me with pride.”
2. Sutton United 2-1 Coventry City, 1989
One of the most celebrated upsets in FA Cup lore occurred in January 1989, when Coventry, a top-flight side and former FA Cup champions, fell to Sutton from the Conference in the third round.
Tony Rains and Matthew Hanlan scored pivotal goals at Gander Green Lane, marking Sutton as the first non-league club to defeat top-tier opposition in decades. Remarkably, they remained the only recent team to achieve this until Luton, also from the National League, took down Norwich in the fourth round in 2013.
3. Chelsea 2-4 Bradford, 2015
It seemed like a routine fourth-round match when Premier League titans Chelsea surged to a two-goal lead against a League One opponent ranked 49 places below them. However, Bradford had different plans, making a stunning comeback with goals from Jon Stead, Filipe Morais, Andy Halliday, and Mark Yeates, leaving a bewildered Jose Mourinho squad in their wake.
4. Crawley Town 3-0 Leeds United, 2021
Another unforgettable upset graced the FA Cup in 2021 when Crawley Town from League Two dismantled Premier League’s Leeds United, who were ranked 62 positions higher. As they advanced to only their third fourth-round appearance in history, Crawley even brought on a reality TV star as a novelty substitute in the final minutes.
5. Newport County 2-1 Leicester City, 2019
The gap of 74 places in the EFL made Newport County anxious before facing recent Premier League champions Leicester City at Rodney Parade in the third round. However, their fears turned to joy when Padraig Amond scored a penalty in the 85th minute, securing an exhilarating win and marking Newport’s first triumph against top-flight opposition in the FA Cup third round since 1963-64.