Rangers manager Steven Gerrard blamed basic defensive errors after their unbeaten European record ended with a 4-3 defeat by Spartak Moscow.
The Light Blues took the lead three times in the first half after an early own goal and strikes from Daniel Candeias and Glenn Middleton, on his second start for the club.
But Rangers had been pegged back by a Lorenzo Melgarejo back-post header and a Connor Goldson own goal, each time after Jon Flanagan had been caught out at left-back.
And they conceded twice in a minute just before the hour mark, when Luiz Adriano headed home on the rebound and Goldson deflected Sofiane Hanni’s strike past Allan McGregor.
It was a first defeat in 12 Europa League matches under Gerrard and saw Rangers slip from top of Group G to third place.
“I’m very disappointed with the result,” the Rangers boss said. “You saw the two sides of our performance.
“We attacked very well, we looked very dangerous and countered very bravely and got our rewards for that.
“We were in control of the game until half-time but football is about levels and if you don’t defend properly high-level teams will punish you and that was the case. We didn’t clear our lines at the right times, at times we weren’t in the right positions. Players who have had a lot of praise, who have done very, very well to get us to this opportunity, just didn’t do the basics well.”