A makeshift Rangers side failed to clear the ever-darkening storm clouds gathering over Ibrox as they lost 2-1 to Hearts in what was their third successive home defeat on Saturday.
With player cuts looming large at the crisis-stricken club, Rangers manager Ally McCoist fielded an unfamiliar side, with youngster Rhys McCabe handed his debut and Andy Little and Salim Kerkar keeping their places in the starting line-up.
Despite this, the new players seemed to gel well together, with Steven Davis firing the home side into the lead in first-half stoppage time.
However, the mood darkened when Ian Black's dipping shot hauled Hearts level before Jamie Hammill put Hearts in front in the 79th minute as he slotted home the rebound after Allan McGregor had saved his initial effort from the penalty spot.
The defeat could prove to be the final appearance for several Rangers players, with administrators likely to announce job cuts on Monday.
It means rivals Celtic's lead at the top has widened to 21 points, despite their 17-game winning run in the Scottish Premier League coming to an end after they were held to a 1-1 draw by Aberdeen at Pittodrie.
Third-placed Motherwell are now within three points of Rangers following their 2-0 win over Dunfermline.
At Ibrox, the visitors were the first to threaten when McGregor could only clear Danny Grainger's cross to Andy Driver, but the Hearts forward's shot from the edge of the box was wildly off-target.
Rangers looked lively going forward and Black had to be alert to clear Sone Aluko's deflected corner off the line before Dorin Goian sent a header straight at Jamie MacDonald from a Davis pass.
McCabe then came close to marking his debut with a goal when his 30-yard strike forced MacDonald into a superb save.
Rangers finally made the breakthrough via a fortuitous goal from their captain, Davis.
The Northern Ireland international got on the end of his fellow countryman Little's cut-back from the by-line to send in a low shot that MacDonald somehow allowed to sneak under his body and into the net.
Hearts got on level terms in the 58th minute. Carlos Bocanegra headed Scott Robinson's initial header off the line but the ball broke to Black, who spotted McGregor off his line and sent a superb shot over his head from 25 yards.
Aluko saw his curling shot held by MacDonald before Little's fierce angled drive was tipped round the post as Rangers pressed forward in search of a winner.
However, it was Hearts who took the lead when they were awarded a controversial penalty after Goian was adjudged to have pulled the shirt of James Beattie.
Hammill's spot-kick was brilliantly saved by McGregor but the rebound broke back to him and he tucked the follow-up under the keeper's body.
At Pittodrie, Celtic took a 28th-minute lead when Charlie Mulgrew picked out Kris Commons and his pass allowed Anthony Stokes to dance around the onrushing Jason Brown and slot the ball home for his 19th goal of the season.
However, the Dons were level a minute before the break when Scott Vernon found Gavin Rae and the midfielder's shot deflected off Celtic debutant Andre Blackman and looped over Fraser Forster into the net.