Rangers suffered a shock 1-0 defeat against Kilmarnock as Marley Watkins' late strike rocked the Scottish title chasers at Rugby Park on Sunday.
After leaders Celtic and second placed Aberdeen shared a 2-2 draw on Sunday, Rangers had a chance to close the gap on their title rivals.
But Philippe Clement's side failed miserably in their bid to take advantage.
Rangers fans held up protest banners in the second half, one of which called for the "mismanagement" of the club to stop.
Killie struck in the 87th minute when Watkins earned his side a first home win of the season, leaving Rangers six points behind Celtic and Aberdeen.
FULL-TIME: Kilmarnock 1-0 Rangers pic.twitter.com/0Lv6a2qF2H
— Rangers Football Club (@RangersFC) October 20, 2024
Rangers will look to get back on track in their Europa League game against Romanian side FCSB at Ibrox on Thursday.
There were fears that Storm Ashley could have an effect on the noon kick-off in Ayrshire, but it was Rangers who were blown away.
Rangers left-back Jefte's header back to Jack Butland in the fourth minute was short and allowed Kyle Vassell to get in front of Robin Propper to toe poke the ball back to Watkins, whose shot was blocked by John Souttar.
The visitors were struggling to find any rhythm, but in the 18th minute former Rangers keeper Robby McCrorie made a good save from Vaclav Cerny's long-range drive.
In the 52nd minute, Cyriel Dessers' drive from 30 yards was tipped round a post by McCrorie for a corner, from which the Rangers striker hit the bar before Propper put the loose ball behind.
McCrorie made saves from James Tavernier and Souttar as Rangers' frustration mounted.
There were cheers from the Rangers fans when Dessers was replaced moments later by Hamza Igamane.
But Rangers were still lacking energy and cohesion, with their title hopes badly dented in the 87th minute.
Watkins pounced, running on to a pass from David Watson and brushing past Souttar to send a shot bouncing beyond Butland.
Igamane was inches away from snatching a stoppage-time leveller from the edge of the area, but Rangers were out of luck.