Rangers kept their hopes of a place in the Europa League knockout stage alive, but it wasn't achieved easily as they drew 1-1 with Brondby.
Steven Gerrard's side were looking to follow up last month's win over Brondby at Ibrox by completing the double over the Danish champions in Group A.
Things turned sour moments before half-time as Leon Balogun headed into his own net to hand the Danish hosts a 1-0 lead.
Subs were needed from boss Gerrard and his introduction of Ianis Hagi and Ryan Kent set up the leveller. Kent slipped through his Romanian teammate to net a vital goal.
Rangers were on a high after their thumping 6-1 win away to Motherwell on Sunday which put them four points clear at the top of the Scottish Premiership.
There were signs in that match that their season is finally set to ignite and they would have hoped to kick on from the Lanarkshire romp.
But now a battle to finish second awaits after Lyon's 2-0 win over Sparta Prague sealed their place as group winners. Rangers are level on four points with Sparta Prague while Brondby have two.
Rangers: McGregor, Tavernier, Goldson, Balogun, Barisic, Davis, Kamara, Arfield, Aribo, Sakala, Morelos.
Subs: McCrorie, McLaughlin, Patterson, Bassey, Lundstram, Hagi, Bacuna, Wright, Roofe, Kelly, Kent.
Keep up to date with all the big match build up, action and reaction in our LIVE blog.
Key Events
The talking points
It wasn't pretty from Rangers but they do enough to claim a point and keep their Europa League hopes alive.
3 talking points as Rangers rescued by triple sub call against Brondby after Ianis Hagi strikes
A battling draw
Full-time! Brondby 1-1 Rangers
The Ibrox side take a point from their Danish trip.
Leon Balogun's header into his own net moments before half-time was a blow but substitutes Kent and Hagi inspired a point, with the latter netting for Gerrard's men.
Kemar Roofe missed a late header to win the game.
Hagi's clinical effort
Tavernier stops the counter
A captain's contribution from the Rangers right-back.
Brondby break on an exposed away defence and the 30-year-old's sliding block prevents a big Danish chance.
Calm after the storm
The intensity of the game has dropped slightly since Rangers' big goal.
But both could do with a win...
A needed moment
Rangers appeared to be toiling in their attacking efforts and changes were needed.
Gerrard has made them and it's lifted his side back into the game through Kent and Hagi.
Goal! Brondby 1-1 Rangers
It's Ianis Hagi after a substitute combination.
Ryan Kent uses his pace to get behind the Brondby midfield and he threads in his Romanian teammate.
Hagi comfortably finds the bottom corner to bring his team back level. A huge goal.
Kent makes his comeback
Aribo working hard
The Nigerian wins the ball high up the park for Rangers but nobody can make use of his good attacking work.
Into the final 20 minutes
Rangers haven't found the final touch in this game, but they'll have to find it fast if they're to take anything from this.
Kamara denied
The Rangers midfielder looked to have had a chance to test the Brondby defence, but his effort is blocked as it soared towards goal.
Gerrard's subs have kicked things up a gear.
You wait an age for one...
And now Lyon are two ahead against Sparta Prague. A long way back for the Czech side now.
Lyon ahead
There's finally a goal in the other Group A game and Lyon have scored to go 1-0 up on Sparta Prague.
Balogun tries to patch things up
Kent moves forward and wins a corner for Rangers with a long-range drive.
Balogun almost makes amends for his own goal but his shot is straight at the keeper.
An almost-instant impact
Ianis Hagi creates room for himself in the final third and tries to thread through Kemar Roofe.
The Rangers striker can't make a connection with the ball but it's better from the away side.
Ryan Kent returns
Gerrard is ringing the changes.
Morelos, Sakala and Arfield all make way as Roofe, Kent and Hagi come on.
It's a new-look forward line and Rangers will hope the return of Kent provides a spark.
Brondby go close
McGregor is the only reason why Brondby are not 2-0 up.
From another Brondby corner, Rangers don't deal with the danger. Tshiembe is allowed to take a touch inside the box but the veteran goalkeeper reacts well to parry.
Cagey start
Rangers are struggling to find any rythm in the final third.
A change may be needed to spark the result needed.
The difference-maker...
Two to ponder
Rangers' game agression has been limited by early bookings for Morelos and Sakala.
If Gerrard feels he needs back-up, Ryan Kent and Kemar Roofe wait on the bench.
Brondby's maiden goal
Just to cap off a poor end for Rangers, it's the first time Brondby have netted in the competition this year.
They didn't have to work hard for it either.
A bitter pill to swallow at the half's end
Set-piece agony and joy
There's been a clear pattern in this game - Brondby and Rangers have both enjoyed their best chances from corners and free-kicks.
Tavernier's crosses have provided away openings but they haven't dealt with one key cross at the other end, and it's why they are behind.
A big half now awaits.
HALF-TIME! Brondby 1-0 Rangers
Rangers looked to be heading in at 0-0 but Brondby go ahead with the final action of the half.
Alfredo Morelos has created a few chances but the hosts have dominated posession, without creating too many chances.
Gerrard may have a different team talk after a late twist.
GOAL! Brondby 1-0 Rangers
A hammer blow for Rangers before half-time as Leon Balogun knocks one into his own net.
Gerrard's team have dealt with corners well up until this point but this will sting.
The ball is not cleared and eventually Balogun heads past McGregor just seconds before the half-time whistle.
Another chance cleared
While holding the majority of possession this half, Brondby have created few chances.
Their latest attempt is a corner easily dealt with by the Rangers defence.
