David Hannah's second half strike put Dundee United into the semi-finals of the Scottish Cup and forced Rangers to face up to the bleak prospect of a trophy-less season.
Now all Dick Advocaat, whose position will now come under intense scrutiny, has to play for is second place in the league and the Champions League place that goes with it.
After the game, the Rangers manager made it clear he still wanted to carry on with his rebuilding plans, and expected to be allowed to do so. Asked whether the cup knockout would make him reconsider his future he replied: "Not at all."
He added: "We know exactly what we are doing. We have to go on. The only thing we can do is again get into the Champions League."
More players are expected to arrive in the coming weeks, although the exact number depends on how many of his current under-achievers he is able to discard.
He said: "Maybe one or two players will come. It has to do with how many players will go." But his future selection problems have intensified once more as Bert Konterman faces a ban following his dismissal for two bookable offences.
Advocaat's severely weakened side failed to muster a single shot on target against a United team who were the better side in the first half and restricted Rangers to a single threatening moment, which saw Tore Andre Flo hook wide under pressure from Craig Easton.
Rangers had the best of the play after the break but it was United who went ahead in the 62nd minute.
Easton crossed and Craig Moore appeared to have got the better of Hamilton in the box.
But the United man was still able to hook the ball back in to the danger zone where Charlie Miller was lurking.
Fernando Ricksen did enough to put him off but the ball continued its path to the onrushing Hannah, who smashed it past the exposed Stefan Klos.
Rangers almost replied with an instant equaliser when Dodds slid the ball across the United box to Allan Johnston at the far post, but he somehow managed to put the ball across Paul Gallacher's exposed goal and wide.
Rangers' chances of retrieving the situation diminished when Konterman was sent off for his second bookable offence after fouling Jamie Buchan.
Rangers had Klos to thank that the scoreline remained at 10. He was required to make two world-class saves to deny Lilley in the space of seconds, with the first an amazing Gordon Banks-style deflection of a header upwards and over the bar.
Dundee Utd: Gallacher, McCunnie, De Vos, Lauchlan, Buchan, Easton, Miller, Griffin, Hannah, Hamilton (Thompson 83), Lilley. Subs Not Used: Combe, Venetis, Naveda, Smith. Goals: Hannah 61. Rangers: Klos, Moore (Malcolm 80), Amoruso, Wilson, Porrini, Ricksen (Carson 71), Ferguson, Konterman, Johnston (Miller 64), Flo, Dodds. Subs Not Used: Christiansen, Kaupilla. Sent Off: Konterman (68). Booked: Konterman, Moore, Amoruso.
Referee: J Underhill (Scotland).