My answer on Quora.
As a Liverpool fan there were two that were gut wrenching. I still have nightmares about them to this day.
1977 FA Cup Final - Those damn white shirts. Source: 1977 FA Cup Final at Wembley Stadium : Manchester United 2 v Liverpool 1...
Manchester United 2 Liverpool 1 - FA Cup Final (1977)
I was only eight years old at the time of this match and watching football on TV in South Africa was a rarity (the country had no TV until 1975). However I was hooked on Liverpool from the moment that I started collecting Football cards. Kevin Keegan was my favourite player and in that season Liverpool repeated their performance from a year earlier by winning the League. The Reds had also made it to the Final of the European Cup which they were destined to win a few days later (3–1 against Borussia Moenchengladbach).
However in an era when domestic cup finals meant a lot more than they do today the FA Cup was key in Liverpool winning a unique treble.
Unfortunately it was not meant to be. Despite dominating possession Alex Stepney was a rock in goals for the Devils and Liverpool were out on the back foot early on in the second half courtesy of a Stuart “Poncho” Pearson strike. Jimmy Case drew level for the good guys (an amazing strike) but only three minutes later Jimmy Greenhoff settled it for the Mancunians. Liverpool did their best to salvage but United held firm.
As for myself it was the first time in my life that I can recall being ‘gutted’ by a sports result. It wasn’t to be the last.
Liverpool 0 Arsenal 2 (Last game of the 88/89 League season)
Arsenal had been great that season, but Liverpool who were the defending champions, had been on a league run that saw them win fifteen and draw three of their last eighteen matches. Indeed they had come back from a slow season start to place themselves in the drivers seat for the title. All that was needed was to avoid losing by two goals to Arsenal at Anfield. Now emotions on Merseyside were in a state of turmoil. The Hillsborough disaster on the 11th of April 1989 had cut a knife through the city. It was a terrible time. The Reds had given the fans something to cheer for.
The Arsenal game stood at 0–0 at half-time. Alan Smith then scored for the Gunners soon after the break but Liverpool held on. Then as the embers dimmed it happened…Michael Thomas connected with a goal that sunk Liverpool…2–0. No time for a reply. Arsenal were League champions (the first time since 1971). Liverpool, by the closest of margins were runners-up.
Liverpool did salvage part of the season though by winning the FA Cup (3–2 over Everton) in a final that was both entertaining and nerve wracking however it was the Thomas strike was acid in the eyes of every Red Supporter . To this day I grow cold thinking about it.
Oddly enough Thomas would later play for Liverpool in the future scoring the opener in the 1992 FA Cup final that saw Liverpool run out as 2–0 winners over Sunderland.
1989 - Football’s closet ever title finish….Football's greatest-ever title finish? Arsenal's 1989 triumph over Liverpool, told by the players
The rollercoaster ride of a football fan. YNWA.
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