Two things spring to mind when compiling the five greatest ever FA Cup semi-finals.

With Oldham’s titanic 3-3 draw with Manchester United in 1990 just missing the cut, the first thought is that United have gifted us a treasure-trove of remarkable FA Cup encounters down the years.

Then comes a question. What kind of madness descended on the competition in the Nineties and can we please see it again sometime soon?   

5) Tottenham 3 Arsenal 1 (1991)

The first ever FA Cup semi-final to be held at Wembley was an all-North London affair with Spurs very much the underdogs coming up against a Gunners side who already had one hand on a league crown. 

With just five minutes on the clock, Terry Venables’ men won a free-kick some distance out, so far away in fact that Arsenal only put two men in their wall. Big mistake.

At the height of Gazza-mania, up stepped the irrepressible Paul Gascoigne to fire home one of the most iconic goals ever scored beneath the famous twin towers. 

A Gary Lineker double ensured a fabulous Arsenal team were denied a possible double courtesy of their neighbours. 

4) Manchester United 2 Arsenal 1 (1999 replay)

United’s FA Cup odds for this season have them as second favourites to lift the cup for the 13th time in their illustrious history.

For drama, and scale, and unforgettable moments however, nothing will ever come close to matching their tenth triumph. 

The final itself was a routine dismissal of Newcastle but fellow heavyweights Arsenal took them all the way in the last four, grinding out a 0-0 draw before this ridiculous replay unfolded at Villa Park.

Understandably, Ryan Giggs’ individual winner takes the plaudits but perhaps it detracts from what else occurred on that feted evening, a game that featured two long-range thunderbolts – from Beckham and Bergkamp – along with a disallowed goal apiece, Roy Keane getting sent off, and a last minute missed penalty. 

3) Fulham 3 Manchester United 5 (1958 replay)

Just 48 days after the Munich Air Disaster, a makeshift United side pulled off a minor miracle in beating an excellent Fulham collective, led by the great Johnny Haynes. 

If that were not extraordinary enough, they had to do it twice-over.

The Reds raced into a three-goal lead only to see their substantial advantage cancelled out as Fulham’s class eventually told. 

Yet somehow, with their manager Matt Busby recuperating in Switzerland, a team mainly made up of reserves found the wherewithal to produce two late goals, booking their place for Wembley. 

2) Chesterfield 3 Middlesbrough 3 (1997)

Stoically mid-table in the third tier, the Spireites embarked on a wonderful cup adventure in the late-Nineties, eventually meeting up with big-spending Middlesbrough in a semi at Old Trafford that is still fondly recalled a quarter of a century on. 

Attempting to become the first team from their division to reach a FA Cup final, Chesterfield surprised a watching nation by going two up before the break. With Boro defender Vladimir Kinder sent off early doors too, they were in dreamland. 

Fabrizio Ravanelli pulled one back and then came the controversy, as a third Spireites goal clearly crossed the line but was ruled out. 

A commendable comeback by the Premier League side meant they were 3-2 ahead with seconds to spare. Cue a Jamie Hewitt looping header that sent a million jaws dropping to the floor. 

1) Crystal Palace 4 Liverpool 3 (1990)

Six months prior, the Reds decimated Palace 9-0 at Anfield so it was par for the course when Ian Rush put them ahead in the early stages.

All of the FA Cup predictions tipped Liverpool for the cup that year, to go with their imminent 18th league title. To go with everything else they won back then. 

A vibrant Palace side though had other ideas, turning the contest around to 2-1 and then refusing to buckle even when John Barnes and co turned on the style to make it 3-2. 

A late equaliser took the game into extra-time and when Alan Pardew nodded home a winner it became very apparent that what was unfolding was a classic for the ages.


 

Stephen Tudor is a freelance football writer and sports enthusiast who only knows slightly less about the beautiful game than you do.

A contributor to FourFourTwo and Forbes, he is a Manchester City fan who was taken to Maine Road as a child because his grandad predicted they would one day be good.