Six times in 17 years they reached the final only to leave empty-handed, the tangerine and black ribbons shoved in a Hampden bin rather than tied on to the famous old trophy. When a popular United fanzine emerged in the late 1980s calling itself The Final Hurdle you didn't need two guesses to work out what the title was referring to.
United had won the Scottish Premier Division title, the League Cup, reached the European Cup semi-final and the UEFA Cup final but seemingly just couldn't win the Scottish Cup. The first United team to do so then would be hailed as heroes forever and so it proved.
Next Tuesday marks the 20th anniversary of United's 1-0 win over Rangers, the result that finally ended all talk of a cup hoodoo.
There was an added poignancy given the goalscorer was Craig Brewster, a local boy who had grown up a United supporter and watched many of those previous losing finals on the Hampden terraces.
Brewster had been released by the Tannadice club as a youth player and had only returned the previous summer after signing from Raith Rovers. The goal was among the simplest he ever scored - a tap-in from a couple of yards - but its significance was huge.
"It was amazing for me as I stood on the touchline or in the stands many times and watched us lose final after final," recalled Brewster of that special day. "So to finally go as a player 20 years ago and face a Rangers side which was going for a double-treble with so much quality in their side and score the winning goal was incredible.
"You don't realise at the time the impact it has on people and here I am 20 years on speaking about it. I was the lucky one to score but the team performance was incredible."
The pinnacle of Brewster's career would also prove a managerial high for Ivan Golac. Like his star striker, the Serb had only signed for the club that season but his innovative coaching style and positive approach were the foundations for that Hampden success in 1994.
"Ivan put into his players a mindset that we were winning this, end of story," added Brewster. "Defeat didn't cross his mind and that was massive psychologically. It was massive that we had also beaten Rangers at Ibrox 3-0. We were 3-0 up after 19 minutes and that had a massive impact as we knew we could beat them.
"It broke the barrier for us. Rangers had won the league about six weeks previously and they were playing games just for the sake of playing games. So they had lost that edge. As a player or manager watching your team you know within the first five minutes if everyone is up for it. We were slamming into tackles and we knew we would perform well."
United head to Celtic Park this weekend for a William Hill Scottish Cup final against St Johnstone. Since the success of the 1994 team there has been one further triumph in 2010 and now Brewster is hoping for a hat trick.
"They can play, as Dundee United are a very good footballing side," he added. "But they know Saints are going to be at them. I just hope it's a good spectacle."