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Rangers failed to capitalise on Scottish Premiership leaders Celtic's dropped points as they had to rely on James Tavernier's stoppage-time penalty to rescue a late draw at Aberdeen.
In a dress rehearsal of next month's Viaplay Cup final, the visitors travelled north nine points adrift of top spot but with two games to spare, knowing that a victory would reduce the deficit to six on Celtic, who were held by Motherwell on Saturday.
But Rangers struggled to deal with the hosts' direct approach in the first half, which brought the first goal as Ester Sokler's simple flick from a punt forward sent in Bojan Miovski to emphatically dispatch his 11th strike of the season.
That came just minutes after Sokler had burst through a similar gap in Rangers' high line, but the Slovenian was denied by the boot of Jack Butland, who got low to deny a Jamie McGrath effort later in an electric opening period.
Miovski's goal woke up Clement's men in an attacking sense, with Danilo having a pair of near-post attempts saved by Kelle Roos either side of the break before the Aberdeen goalkeeper reacted superbly to Leon Balogun's close-range header.
The Ibrox club ramped up the pressure in the final quarter of the game, smashing the crossbar twice in as many minutes as a stunning Tom Lawrence strike was followed by another Balogun header.
But it looked like a goal would never come until Stefan Gartenmann's daft shirt pull on Connor Goldson resulted in a spot-kick being awarded after a VAR review.
Rangers captain Tavernier converted by burying straight down the middle to extend manager Philippe Clement's unbeaten start to eight games, but the Ibrox boss will know that this is an opportunity missed against an Aberdeen side who remain ninth.
The midfielder (right) looked back to his best in a fantastic first-half performance, showing superb quality on the ball by creating three chances for his side
Is it possible for a draw to feel like a defeat for both teams? That could be the case here.
Aberdeen can be proud of their response to the 6-0 drubbing they were handed by Celtic a fortnight ago, though, and this will give them extra belief heading to Hampden next month as they now have two wins and a draw in their last four games against Sunday's opponents.
Striker turned pundit Kris Boyd suggested that Barry Robson would have no problem getting his players fired up to face Rangers - a view that is shared by more than a few Ibrox fans.
But perhaps it says more about the Govan side's mentality that they have now dropped four points to a team who currently sit seven places and 15 points behind them after just 13 games.
Rangers almost let the chance of closing the gap slip against Hearts last month, but two stoppage-time goals bailed them out. They couldn't do it this time, although we would have seen a remarkable repeat had Sam Lammers steered a header beyond Roos in the dying seconds.
Overall, their inability to deal with Aberdeen's direct play and a lack of ruthlessness in front of goal creeping back in will be the immediate concerns for Clement, whose side failed to score from open play with over 70% possession.
Both sides are in continental action on Thursday as Aberdeen travel to HJK Helsinki (17:45 GMT) in the Conference League before Rangers host Aris Limassol (20:00) in the Europa League.
