Steven Gerrard’s Rangers side have looked dominant in Scottish football so far this season but they will not earn themselves a domestic treble after they were defeated 3-2 by St Mirren on Wednesday night.
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.
1. 2016 Betfred Cup semi-final
A late Moussa Dembele goal saw Celtic advance to the final at the expense of their rivals, who were a tad fortunate to still be in the match before the 87th minute strike. Photo: SNS Group Alan Harvey
2. 2016/17 Scottish Cup semi-final
Callum McGregor and Scott Sinclair netted in a comfortable win for Brendan Rodgers' side. Rangers, by this point, were managed by Pedro Caixinha after Mark Warburton left the club. Photo: SNS Group Craig Williamson
3. 2017 Betfred Cup semi-final
Louis Moult netted twice to pull off an upset for Stephen Robinson's men at the expense of Caixinha's side. The manager would later complain about Motherwell's physical approach. Photo: SNS Group Craig Foy
4. 2017-18 Scottish Cup semi-final
Frustrations boiled over in this game under the stewardship of Graeme Murty. Andy Halliday angrily reacted to being taken off, while Greg Docherty and Alfredo Morelos almost came to blows late in the game. Photo: SNS Group Rob Casey