Rangers were booed at Ibrox as calamity defending against Club Brugge left their Champions League hopes in the balance after a 3-1 first-leg defeat in their play-off tie.
A bit of luck against Panathinaikos and Viktoria Plzen gave the Gers hope of a return to European football’s elite club competition, but simple mistakes left them 2-0 down after just seven minutes.
Nasser Djiga failed to deal with a bouncing ball inside his half, allowing Romeo Vermant to race in and dink the ball over Jack Butland from 30 yards.
They switched off again leaving Jorne Spileers unmarked to send the ball in from a corner, with some home fans then heading for the exits when Brandon Mechele fired in a brilliant third.
Jayden Meghoma was handed his Rangers debut and his cross set up Danilo to pull a goal back after the break.
Djeidi Gassama thought he had pulled them back into the tie late on, but his goal was disallowed after a VAR review, with goalkeeper Simon Mignolet judged to have two hands on the ball when Gassama prodded it over the line.
Is Champions League football out of reach for another season?
Cheers quickly turned to jeers at Ibrox once again as a horror mistake by Djiga allowed Tzolis’ pass to give Vermant an easy finish to stun everyone inside the ground.
The Gers fans were still getting their head around that early goal when Tzolis’ corner from the right was knocked past Butland by the unmarked Spileers from 12 yards.
The boos that rang round the ground intensified when Mechele, making his 500th appearance for Brugge, stepped all too easily in front of Danilo just outside the Rangers box and gave Butland no chance with an arrowed right-footed drive to put the visitors three up in 20 minutes.
Light Blues midfielder Joe Rothwell clipped the outside of a post with a free-kick from 25 yards in the 26th minute but it was not the signal for a comeback as Butland had to brilliantly beat away a drive from Carlos Forbes, with the home defence again split open.
A three-goal deficit at the break left the Gers support in a state of shock but they got a lifeline when Danilo slid in to convert an enticing cross from Meghoma.
Brugge stepped up the pace and amid a flurry of corners, Butland made a fine from Joel Ordonez.
Gassama had the ball in the Brugge net in the 78th minute but French referee Francois Letexier was asked by VAR to check his pitchside monitor and quickly decided that Mignolet had the ball in his hands before it was bundled into the net.
The Light Blues second-half display was heartening but it was a nightmare first 20 minutes which keeps the spotlight on Russell Martin for the wrong reasons.