The most iconic FA Cup final moments are forever seared in time. From Jim Montgomerie’s double-save in 1973, to Kevin Moran’s sending off in 1985.

From Keith Houchen’s diving header in 1987, to Steven Gerrard’s last-gasp piledriver in 2006.

These are cultural landmarks that define what the world’s oldest footballing competition means to every one of us, as significant as wars and jubilees. 

The following five unforgettable highlights and lowlights deserve to be put in that same canon.   

Willie Young’s Professional Foul

There is a direct lineage from Moran’s red card in 1985, for scything down Peter Reid when the last man, to Arsenal’s Young doing likewise five years earlier and only receiving a booking.

At 17, West Ham’s Paul Allen was the youngest player to ever appear in a FA Cup final and via some clever footwork found himself clean through against the Gunners, a life-defining act of glory in his grasp.

Young though – brutal in appearance and brutal in demeanour – had other ideas, callously tripping the teenager, the ball far beyond his reach. 

So appalled was a watching nation that the incident brought about a change in the rules, with the FA ushering in a directive that a ‘professional foul’ could be punished by instant dismissal.


Di Matteo’s Howitzer

The duel between Chelsea and Middlesbrough promised to be a continental affair, in an era when this was still a novelty, featuring Juninho and Ravanelli in red, and Zola and Vialli in blue. There’s some goals in that quartet.

It was another Italian who stole the show however, with Roberto Di Matteo firing in a thunderbolt from range just 43 seconds in. 

In hindsight, the earliness of the strike detracts from just how good the goal was, the midfielder picking up possession well into his own half before scurrying forward uncontested.

From a full thirty yards out he unleashed a howitzer that flew directly above the keeper’s flailing reach.


Watson Wins It

Much more should be made of the fact that in 2013 Wigan Athletic won the FA Cup and did so as huge underdogs against Manchester City, scoring the winning goal in the 91st minute. 

That Ben Watson’s last-minute header has merely become an endearing curio in the competition’s back-catalogue instead of being burnished in legend is reflective of how the FA Cup has sadly lost some of its allure and sense of romance in recent times. 

Had this occurred in the Eighties films would be made about it. 


It’s Only Parlour

For much of 2022/23, Arsenal were favourites in the Premier League winner odds, only to see their challenge slip away.

There was no suggestion of ‘bottling’ however back in 2002, and with the title already sewn up, the Gunners headed to the Millenium Stadium with a double in their sights. In their way was a brilliant Chelsea collective.

Naturally enough, with the final featuring two elite sides, there was little to separate them for the most part, but then in the 70th minute Ray Parlour picked up the ball and was surprised to see opposition defenders stand off him.  

“It’s alright. It’s only Parlour,” Tom Lovejoy said while doing fan commentary, while Jimmy-Floyd Hasselbaink has subsequently admitted he relaxed when seeing who was lining up to shoot from distance. 

The maligned Arsenal midfielder proceeded to curl an absolute beauty into the top corner.


Angry Mackems

According to our Premier League predictions, Newcastle are going to be in the running to win silverware next season but back in 1999 trips to Wembley were very much a novelty.

A final against a treble-chasing Manchester United was their best chance to win a trophy for generations. 

Perhaps this explains what prompted Sunderland midfielder – but life-long Magpies supporter – Lee Clark to attend the game wearing a t-shirt emblazoned with ‘SMB’

The S stands for Sad. The M stands for Mackem. The B queries their parentage.

Clark never played for Sunderland again.


 

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.