Despite taking an early lead through Connor Goldson and finding an unlikely equaliser in the 88th minute thanks to Steven Davis, the Light Blues were finally undone by a Conor McCarthy goal after Jamie McGrath had scored twice to turn the match on its head.
At this point, it looks like it will still be a successful season for the Ibrox side, who hold a 13-point lead at the top of the Scottish Premiership table and are in the knockout stages of the Europa League.
However, last night was a familiar disappointment to fans who are still waiting on their favourites to win a major trophy since returning to the top flight in 2016.
Here are all nine exits that Rangers have suffered in cup competitions since the 2016 Scottish Cup final defeat to Hibs.
9. Betfred Cup 2020-21 quarter-final
Rangers' undefeated start to the 2020/21 season ends in Paisley as the hosts fight back from an early opener and a late equaliser to win the tie in stoppage time. Photo: Craig Williamson - SNS Group