Dundee United celebrated their first victory over Rangers in almost three years thanks to first-half goals from Mark Kerr and Andy McLaren.
The result saw last year's Treble winners fall even further behind Celtic in a championship race that has already seen bookies pay up on the Hoops, who moved 16 points clear by hammering Livingston at the same time.
The hundreds of Rangers fans whose journey to Dundee was delayed by a road closure must have wished they were back in a traffic jam when Kerr and McLaren hammered two more nails into their coffin with a goal each in a three-minute
spell.
Rangers manager Alex McLeish must now somehow conjure up a cup win at Celtic next week to prevent the campaign's life support system being turned off altogether.
On Friday, he was bemoaning the fact that no team is afraid to take on Rangers on their own ground any more and Ian McCall's United, whose own season had failed to live up to pre-season hype before this game, offered plenty of proof that he was correct.
Rangers had created early chances with the recalled Michael Mols heading over and Mikel Arteta denied by a triple combination of a deflection off a defender, goalkeeper Paul Gallacher's outstretched hand and an upright.
But United's reply was to net twice in three minutes and Kerr's opener was a stunner, a drive from the edge of the area that bounced over the line off the crossbar.
McLaren had supplied the cross from the left that the Rangers backline had been unable to clear properly as Jim McIntyre challenged Fernando Ricksen and the ex-Killie man netted the second.
That was a shock for the Rangers defence as they allowed Barry Robson's corner to find McLaren at the back post for the ex-Scotland cap to bundle the ball home from embarrassingly close range.
Emerson scuffed a shot wide and Frank de Boer saw a free-kick deflected away off Chris Innes as Rangers sought a route back into the match.
But it could have been much worse for the fallen champions had not McLaren's shot on the turn not taken such a deflection off Frank de Boer. That took it over Stefan Klos but also high enough to bounce to safety of the crossbar.
Whether McLeish indulged in some good old-fashioned tea-cup throwing at the break is not known but he made two changes with Arteta and Emerson hooked and Steven Thompson, the ex-United striker, and Dundee lad Maurice Ross sent on.
A third and final change followed just 12 minutes later when Gavin Rae was able to make only his second appearance for Rangers since his transfer-window switch from Dundee, with Christian Nerlinger making way.
The changes turned out to be cosmetic however as few chances of note were created by either side in the second period, with United content to protect their good earlier work and Rangers already worrying about what might happen at
Parkhead, the scene of a 3-0 defeat last month, next week.
February 29th comes around only once every four years but poor performances away from Ibrox are arriving much too regularly for the liking of the Rangers faithful and McLeish, who must be praying for a change of luck at Celtic next week and in the transfer market in the summer.
Tannadice joined Pittodrie, East End Park, Fir Park and Almondvale on the list of venues where Celtic have won and Rangers have not this season.
Skipper Craig Moore became an additional worry when he was hurt bailing out Ricksen with a collision of a challenge on Robson after the Dutchman had gifted away possession.
The Australian hobbled back on after treatment for a leg injury, with Michael Ball having been booked in the 79th minute for upending Robson, who was denied a
stoppage-time third only by an excellent block from Klos, the one Ranger who has maintained last season's performances through this sorry campaign.
That was of no concern to ex-Rangers player McCall, who had at last tasted victory against the Old Firm having been denied a point at Celtic earlier in the month by a dubious penalty.
Teams
Dundee Utd Gallacher, Wilson, Innes, McCracken, Archibald,
McLaren, Kerr, McInnes, Robson, Miller, McIntyre.
Subs Not Used: Jarvie, Samuel, Duff, Easton, Scotland.
Goals: Kerr 31, McLaren 34.
Rangers Klos, Ricksen, Moore, Frank de Boer, Ball, Capucho,
Arteta (Thompson 45), Emerson (Ross 45), Nerlinger (Rae 57),
Ronald de Boer, Mols.
Subs Not Used: McGregor, Namouchi.
Booked: Ball.
Att: 10,496
Ref: J Underhill (Scotland).