Rangers' Europa League hope took a significant hit as the Gers fell to a 1-0 defeat to Braga in the Estadio Municipal de Braga in the first leg of their quarterfinals clash on Thursday.
Fresh from watching their Scottish Premiership hopes fade with a home loss to rivals Celtic on Sunday, Rangers targeted a positive response against the Portuguese.
But Abel Ruiz's first-half strike proved the difference on a disappointing night for the Light Blues.
How it happened
Following his poor performance in the Old Firm derby at the Ibrox on Sunday, Joe Aribo dropped to the bench as manager Giovanni van Bronckhorst ran the changes against the Primeira Liga side.
Leon Balogun, though, retained his spot at the heart of the defence while Calvin Bassey slotted in at left full-back.
Still, Braga were the better side in the first half, putting together neat passes and having a goal disclosed by VAR.
And when the home team broke the deadline four minutes before the break, it came off Balogun's mistake.
The veteran Nigerian defender got a weak touch to Couto's flicked pass on the edge of the Rangers box, which allowed Abel Ruiz to fire past goalkeeper McGregor at his near post.
Balogun lasted 15 minutes into the second half before van Bronckhorst hauled him off for Burna Barisic. Aribo also entered the fray about the same time as Rangers looked for a sharp response.
Despite the introduction of the Super Eagles midfielder, the Scottish champions failed to create any chance of note in the second half as Braga's defence withstood the visitors' weak attack.
On one rare occasion that Bassey made a Beckenbauer-esque surge from defence to set up a Rangers attack and force a corner, Goldson made a mess of a free header from a fine Tavernier delivery.
And that was that as the Scots lost by the odd goal to the same side they knocked out of this competition two years ago.
What next?
It is not over yet for the Light Blues as they can still advance to the semifinals with a two-goal win over Braga in the return leg at the Ibrox next week.
There is, however, the immediate matter of the Premiership, where Rangers trail leaders by a massive six points.
The Light Blues make the trip to the SMISA Stadium in Paisley on Sunday to confront St Mirren.
