Rangers were handed their first European defeat of the season as they lost 4-3 to Spartak Moscow, but still remain second in Group G.
Roman Eremenko’s own goal handed the visitors an early lead, but they were pegged back when Lorenzo Melgarejo headed home on 22 minutes.
Daniel Candeias’ strike on 27 minutes was cancelled out by Connor Goldson’s own goal, but the Gers did have the lead at half-time when teenager Glenn Middleton rifled home.
Spartak came from behind, once again, and scored two goals in the space of 69 seconds through Luiz Adriano and Sofiane Hanni.
Rangers struck the post in the third minute of additional time through Nikola Katić, but the visitors were edged out in Russia.
Steven Gerrard made five changes from the team that beat St Mirren at the weekend, Middleton was handed his first European start and made an instant impact.
Own goal hands Rangers the perfect start
Roman Zobnin fired narrowly wide for the hosts early on, but the visitors found themselves ahead after just five minutes in Russia.
Middleton’s fantastic corner drifted into the box and Eremenko inadvertently headed into his own net, under pressure from Lassana Coulibaly.
However, despite going behind early on, the hosts responded well and went close through Salvatore Bocchetti and then Fernando on 14 minutes.
Spartak drew level shortly after, their pressure paid off as Ivelin Popov’s cross from the right was headed home, at the back post, by Melgarejo.
Candeias lost his man for the goal, but certainly made up for it five minutes later when he put his side back ahead.
Jon Flanagan’s pass over the top was brought down exquisitely by Candeias. He took a touch to bring the ball down and then fired into the bottom corner.
Middleton puts Gers ahead at half-time
Middleton’s low cross was almost turned into his own net by Bocchetti on 33 minutes, but it was at the other end where Goldson scored an own goal.
Popov’s through ball was perfectly weighted for Nikolai Rasskazov, whose low cross deflected off Goldson’s left foot and past a helpless Allan McGregor.
The Gers bounced back and closed out the half strongly. Alfredo Morelos’ heavy touch turned into a brilliant through ball for Middleton on 41 minutes and the teenager produced an excellent finish.
Gerrard’s side thought they had a two-goal cushion, right at the end of the half. A quick counter attack finished with Morelos finding the back of the net, but the goal was ruled out for offside.
Hosts ahead after two goals in two minutes
Just two minutes after half-time, Spartak went close to drawing level, but found Rangers ‘keeper McGregor in fine form.
The hosts did manage to draw level for a third time, just before the hour mark, after Flanagan gave the ball away cheaply on the edge of the area.
Eremenko’s cross was flicked on by Hanni and saved by the legs of McGregor, but the rebound was headed powerfully into the net by Adriano.
Just 69 seconds after that, the home side stunned Rangers and took the lead for the first time.
Spartak broke with pace, Hanni driving from the halfway line and then firing at goal, his effort took a wicked deflection off Goldson and flew into the net.
The visitors were stunned and could’ve found themselves further behind when Eremenko headed off the crossbar and then had his rebound saved superbly by McGregor on 74 minutes.
Katić strikes post in injury time
Time was running out for an equaliser for the Gers, who, deep into injury time, struck went within inches of snatching a point.
Middleton’s corner swung to the back post and Katić bundled the ball onto the post before Spartak scrambled the ball clear.
Just two points separate top and bottom in the group now and next up for Rangers is a trip to Austria to face Rapid Vienna.