Rangers have been knocked out of the Champions League after a tough night in Eindhoven saw them fall to a 5-1 defeat against PSV.
Ismael Saibari scored twice and Luuk De Jong netted the third just after James Tavernier had brought one back for the Ibrox side in the crunch second-leg clash on Wednesday.
Joey Veerman then secured the win before a disastrous own goal from Connor Goldson put the icing on the cake of the 7-3 aggregate win that puts the Dutch side in Thursday’s group stage draw.
Rangers will now drop into the Europa League group stages as they return to the competition they reached the final of in 2022.
Michael Beale made two changes from his team that drew 2-2 at Ibrox last week with John Lundstram and goal-scoring hero Rabbi Matondo replacing Abdallah Sima and Ryan Jack.
The home side had the best of the opening exchanges but the Rangers defence managed to keep them at bay for the first half-hour.
The best chance for the visitors in the first-half fell to Dessers but his shot was just wide of the post after a long ball from Goldson split the PSV defence open.
Jack Butland then made a great stop to keep the score at 0-0 but the home support never had to wait much longer for the opener when Ismael Saibari scored a header to make it 1-0 with ten minutes of the half remaining.
The Eredivisie side started to turn the screw after the goal had a few chances to double their lead before the break with the best of the lot falling to Bakayoko in first-half injury-time but he skied his effort high and wide of Butland’s goals.
Rangers looked to be just hanging on to the one goal deficit when the referee blew for half-time after a dominant first 45 for PSV.
Peter Bosz’s side started the second in the same way finished the first and kept Beale’s side under the cosh as they looked to put the tie to bed.
And they went 2-0 up on the night and 4-2 on aggregate when Saibari scored his second of the night to give them a commanding lead.
Rangers called for the cavalry and put on Danilo and Sam Lammers in an attempt to salvage something from the game.
And Lammers was involved when they got one back against the run of play when captain James Tavernier done what he does so often in big moments when he arrived at the back post to make it 2-1 and get right back in it.
But only two minutes had past when PSV captain De Jong settled the nerves of the home support when he headed past Butland to retain their two-goal lead with 25 minutes left on the clock.
The former Barcelona forward was left unmarked in the box from a corner and he connected with an expertly timed header to make it 3-1 on the night and 5-3 on aggregate.
Bakayoko then came close to putting the game to bed, but Butland done well to keep it out with a one-handed save.
Matondo was then inches away from throwing Rangers a lifeline with 15 minutes left but his effort struck the post after a jinking run from the Welsh winger.
And the game was put well and truly beyond them just moments later when PSV went up the other end and Joey Veerman slotted home to make it 4-1 and secure the Dutch side’s place in Thursday’s group stage draw.
It was 5-1 soon after a calamitous moment for the Rangers defence when Goldson’s misplaced back-pass rolled into his own net to seal a thumping result for PSV.
It very nearly got worse with five minutes left and Jack Butland was to thank for keeping the score at five.