They played the last 21 minutes with only 10 men after Bert Konterman was sent off for two bookable offences and that just rubbed salt into the wounds. It really was a shocking night and it was a long journey home for the Rangers fans who had made the trip.
With the SPL title realistically out of reach and having already made an exit in the CIS Insurance Cup, the Ibrox men were hoping to finish the season with a third successive Tennent’s Scottish Cuip triumph but there was never much likelihood of it.
Ravaged by injuries – there were 11 first team players unavailable – Rangers were woefully short of ideas or a cutting edge and while United were only marginally better in a poor match they were worth their win.
The task facing Dick Advocaat now is quite simple. Rangers have to finish second to gain an entry into next season’s Champions League.
United looked more adventurous and more hungry in their approach and they had Rangers in trouble after only eight minutes. Sergio Porrini let Craig Easton get away from him and the midfielder set up Jim Hamilton whose shot was blocked away for a corner by Craig Moore.
That said, there was an explosive opening when United centreback Jim Lauchlan followed through on Barry Ferguson after just two minutes and caught the Rangers skipper on the shin with his studs ripping through Ferguson’s sock.
Fortunately Ferguson was able to continue after four minutes of treatment but the Rangers bench must have been worried the injury jinx had spread to their captain.
Of course, Charlie Miller was up against his old team again and his trickery proved too much for Bert Konterman who fouled him twice in the space of a minute and he was cautioned for the second challenge in 16 minutes.
There were more problems in 19 minutes when Easton whipped in a cross from the right and Davie Hannah got in front of the Rangers defence but sent his header wide of Stefan Klos’s left hand post.
It just seemed a real slog for the Cup holders who struggled to create anything and it was United who came close to scoring again in 41 minutes.
Easton was the instigator with an excellent pass for Derek Lilley, who had escaped the attention of Lorenzo Amoruso, who had otherwise been Rangers’ best defender.
Lilley raced into the box in 41 minutes but Klos cleverly narrowed the angle and made an excellent blocking save, to keep Rangers’ goal intact – not for the first time this season.
Four minutes before that Moore became the second Ranger to be booked for a late challenge on Hannah and Dick Advocaat was clearly not best pleased at half-time.
There was a glimmer of hope that things might get better when Barry Ferguson played an excellent ball in for Billy Dodds in 50 minutes but Lauchlan made a vital challenge just as the Rangers striker was about to let fly.
A glimmer was all it was, though, as United took the lead in 61 minutes in a move which caught the Rangers defence all over the place and eight minutes after that Rangers were reduced to 10 men.
It was youngster Jamie McCunnie who started the move with a cross from the right which fell for Jim Hamilton. He hooked the ball over his head and Miller had a shot blocked but it broke for Hannah who hammered a left foot volley into the left corner.
Rangers were up against it but there was worse to come when Konterman was sent off for his second yellow card offence when he tripped Jamie Buchan in 69 minutes.
The Ibrox side’s grip of the Cup was slipping and Advocaat tried desperately to change the situation by bringing on Kenny Miller and young Steven Carson but it had little effect.
Understrength and lacking in ideas, Rangers never looked like they were capable of rescuing the tie. Indeed, had it not been for the incredible agility of Klos United would have finished more emphatic winners.
The German keeper made two astonishing saves from Derek Lilley in the dying moments, but it was scant consolation for another desperately disappointing chapter in what has been the season from hell.
Now Advocaat has to raise his troops for Wednesday’s SPL meeting with Dundee at Ibrox as he tries to salvage something from the campaign, namely second place in the league.
DUNDEE UNITED: Gallacher; McCunnie, Lauchlan, de Vos, Buchan; Hannah, Miller, Griffin, Easton; Hamilton (Thompson 83), Lilley. Subs not used – Combe, Venetis, Naveda, Smith.
Bookings: None
RANGERS: Klos; Moore (Malcolm 81), Wilson, Amoruso, Porrini; Ricksen (Carson 71), Konterman, Ferguson, Johnston (Miller 64); Dodds, Flo. Subs not used – Christiansen, Kauppila.
Sent off: Konterman (69)
Bookings: Moore (37) Amoruso (82)
Ref: John Underhill
Att: 11,793
Man of the match: Stefan Klos.
Moment of the match: There just wasn’t one.