Rangers’ recent regression continued with a grim goalless draw at Dundee which further dented their increasingly-fragile cinch Premiership title hopes.

The Ibrox side lost for the first time ever against Ross County on Sunday in the poorest performance since boss Philippe Clement took over last October and the Gers boss was looking for a reaction against the Dark Blues.

In a game played at the third time of asking after the Dens Park pitch was twice ruled unplayable, there was no improvement against a Dundee side who impressed.

The travelling Gers fans urged their team on after the break but they lacked imagination and guile and again heard boos at the final whistle.

With five post-split matches remaining including a trip to Celtic Park, the Light Blues are three points behind the Hoops at the top of the table and have hit the skids at the wrong time.

Rangers will now prepare for the Scottish Gas Scottish Cup semi-final against Hearts at Hampden Park on Sunday with newly-acquired trepidation.

Tony Docherty’s Dundee, who commendably clinched a top-six place on their return to the top flight, are now three points behind fifth-placed St Mirren and they deserved their point.

It is now just two wins in eight in all competitions for Clement’s stumbling side.

Utility player Dujon Sterling, midfielder Tom Lawrence and striker Kemar Roofe returned to the side with the latter making his first start since December 20 as Borna Barisic, Kieran Dowell and Cyriel Dessers dropped to the bench.

Ricki Lamie, Owen Dodgson and Malachi Boateng were back for the Taysiders, who came close to scoring within a minute when Boateng’s low drive just escaped Ibrox keeper Jack Butland’s right-hand post.

Dundee skipper Joe Shaughnessy limped off after 10 minutes to be replaced by Antonio Portales before Gers attacker Abdallah Sima outstripped the home defence but his low drive was blocked by the foot of Jon McCracken, the Dundee keeper saving another effort from the Brighton loanee moments later.

Dundee played the better football. In the 22nd minute Butland parried a Luke McCowan free-kick from 25 yards and Scott Tiffoney got to the rebound first to help it on to Amadou Bakayoko to knock over the line from a yard out but the offside flag went up.

Rangers toiled, threatening only occasionally.

McCracken pushed a curling free-kick from Gers skipper James Tavernier round the post then saved a Connor Goldson header from the resulting corner but it was the more composed and fluid home side who were applauded off at the break.

Rangers stepped up the tempo at the start of the second half but a spark of creativity was absent and Dundee’s defending was organised.

In the 56th minute, Clement tried a shake-up and Dessers, Dowell and Rabbi Matondo replaced Roofe, Todd Cantwell and Fabio Silva and McCracken soon had to save from Lawrence’s drive from a tight angle.

McCracken pulled off a fine save from Dessers’ curling shot as the Dees defence were stretched for once and held a tame Tavernier header but it was mostly huffing and puffing from the visitors while Dundee were always a threat.

Worryingly for Gers fans, their side have suffered a dip in form at the wrong time of the season.

Rangers twice surrendered the lead to draw the first leg of their Europa League last-16 tie against Benfica 2-2.

Philippe Clement’s squad was hit by injuries but returning midfielder Tom Lawrence gave the visitors a dramatic early lead with a header before Angel Di Maria levelled with a penalty kick in first-half added time after VAR intervened to highlight that Gers defender John Souttar had used his arm inside the box.

Light Blues’ utility player Dujon Sterling restored the lead in the fifth of five minutes of added time with his first career goal only for Gers defender Connor Goldson to head into his own goal midway through the second half to take the tie back to Glasgow next Thursday night level.

Much of the pre-match talk was around Clement’s limited options in attack. He was without the services of four injured wingers – Abdallah Sima, Scott Wright, Rabbi Matondo and Oscar Cortes – albeit the latter is not in the European squad. With Ross McCausland only fit to start on the bench, it meant no natural width in attack.

Portuguese attacker Fabio Silva, who spent two seasons with Benfica as a youth player, supported main striker Cyriel Dessers from the left with Sterling working off the right.

Under-pressure home boss Roger Schmidt was looking for his side to bounce back from their 5-0 thrashing by title rivals Porto at the weekend and he had a host of big names in the starting line-up including Argentina World Cup winners Nicolas Otamendi and Di Maria.

Around 3,500 Rangers fans were in position to see Gers goalkeeper Jack Butland make an early save at his near post from David Neres’ drive.

And moments later they were off their seats cheering when Silva sent Mohamed Diomande free inside the box and he lifted the ball for the in-rushing Lawrence to head down past diving keeper Anatoliy Trubin.

Butland then made a double save, first from Neres and then from striker Arthur Cabral from the loose ball, albeit his effort had been partially blocked by Souttar.

However, after VAR Marco Fritz intervened following another Benfica corner, the Gers defender was adjudged by referee German referee Tobias Stieler to have hit the ball with his arm as he defended the delivery and Di María sent Butland the wrong way with his assured penalty.

There was more first-half drama to come in the final minute of the five added when Sterling, signed from Chelsea in the summer, stole in to convert a deflected Silva cross from close range, with a VAR check confirming his landmark goal.

Both sides went for more goals from the start of the second half, with Cabral heading wide at the back post from a Rafa Silva cross before Trubin blocked a Silva effort at the other end.

However, Benfica were level again in the 67th minute when Di Maria floated in a free-kick from 35 yards and Goldson stretched to clear but only sent it past Butland.

The home side sensed a winner was there for them and Di Maria somehow missed the target from 12 yards.

In the 77th minute Kemar Roofe, Ryan Jack and Cole McKinnon took over from Dessers, Lawrence and Sterling but Benfica’s steady pressure continued to the final whistle.

The return game promises more thrills and spills but Rangers will look to complete the job in Govan.

Rangers maintained their advantage over Celtic at the top of the cinch Premiership but only after a hard-fought 2-1 comeback win over Kilmarnock at Rugby Park.

Killie wide-man Danny Armstrong scored from the spot in the 11th minute of an energetic first half and Derek McInnes’ side were worth their interval lead.

The Gers had to dig deep and captain James Tavernier levelled in the 55th minute with a trademark free-kick before midfielder Tom Lawrence netted with a fine finish just four minutes later as the visitors reasserted themselves.

With 10 league games remaining – five before the split – Philippe Clement’s side are two points ahead of Celtic, who demolished Dundee 7-1 at Parkhead to keep hot on the heels of the Govan men.

The visitors had racked up 10 wins in a row with a 5-0 win over Hearts at the weekend, including a 3-1 win over Killie on January 2, the only defeat for the Ayrshire outfit in their last 14 outings.

Clement had noted the vagaries of the artificial surface and again tinkered with his squad to suit, making three changes with Borna Barisic, Ross McCausland and Fabio Silva coming back in while the home side were unchanged.

Silva had the first effort on goal after five minutes, his close-range shot deflected for a corner from which Rangers defender Connor Goldson’s header was pushed behind by Killie keeper Will Dennis.

Liam Donnelly came close with a header at the other end as Killie responded but moments later John Lundstram blocked an Armstrong cross with his arm and referee David Dickinson pointed to the spot.

Armstrong confidently beat Jack Butland with his penalty and yet another upset was on the cards.

Clement’s men appeared ill at ease as the route-one first-half unfolded further and Kilmarnock continued chasing and harrying.

There was some controversy in the 40th minute when Mohamed Diomande appeared to prevent Liam Polworth from cleanly latching on to his short pass, but Dickinson played on and was not required by VAR to check his pitchside monitor, to the ire of the home players and supporters.

Cyriel Dessers and Ridvan Yilmaz replaced Silva and Barisic for the start of the second half – Dujon Sterling would replace McCausland – but Butland soon had to make a fine one-handed save to prevent Matty Kennedy stroking in a second from six yards out.

Kilmarnock paid for that miss after defender Lewis Mayo fouled Lawrence 25 yards from goal, with Tavernier stepping up to send his curling shot past the diving Dennis.

Rain continued to swirl around the ground as Rangers went for the second, which came when Lawrence pounced on a loose ball at the edge of the box and guided his shot low past Dennis and into the far corner for his first goal of the season, sparking wild scenes of delight in the stand behind the goal which housed the visiting fans, some of whom spilled out.

The game had swung towards the rejuvenated Ibrox men and Dessers hit the bar from a Tavernier corner.

In the 70th minute, Oscar Cortes limped off with what looked like a hamstring problem to be replaced by Scott Wright and the game was still in the balance.

Diomande curled a shot past the far post from 16 yards as play sped from end to end and Dessers got tangled up as he tried to capitalise on a mistake by Killie centre-back Stuart Findlay.

Six minutes were added on but there were no more goals which meant a crucial three points for Rangers, but Celtic’s stunning win over Dundee confirmed there is still plenty left in the title race.

Philippe Clement was facing the possibility of more injury woes after Connor Goldson pulled up in Rangers’ 2-0 win over Motherwell at Fir Park.

The boss was without Nico Raskin, Tom Lawrence, Ryan Jack, Borna Barisic, Ben Davies, John Lundstram, Kemar Roofe, Jose Cifuentes and Danilo for the trip to Lanarkshire.

Early goals from Kieran Dowell and Todd Cantwell took the Light Blues to within two points of cinch Premiership leaders Celtic, with a game in hand, but veteran defender Goldson was replaced by John Souttar in the 86th minute and ahead of the home game against Ross County on Wednesday before taking on Celtic at Parkhead on December 30.

Clement admitted he was a “little bit fed up” talking about injuries but on Goldson he said: “We will see tomorrow. He felt something at the end of the game but we will see tomorrow.

“We take it day by day what the situation is and what the fitness of the players is. It’s difficult to plan in advance so I’m living from day to day.

“For me, the most pleasing thing is that despite having nine injured players, the structure stays, with two players in midfield who are not used to playing there.

“You don’t see the difference. The team is really focused and concentrated to do the job together. Everybody knows what we are doing, we keep clean sheets and we keep winning games by being dominant.

“In the circumstances of today, we played a really good first half with good attacking football, two good goals, several good chances.

“In the second half, the wind was even harder and the difficulty was that it was really turning in the stadium. It was difficult to play the good quality that we want to bring.

“As long as there is a two-goal difference then the other team always feels it is in a game, and they fought and put a lot of balls in the box.

“We were really concentrated and good in the duels. I don’t think they had one shot on goal from the Motherwell side. We controlled the game well and we got three deserved points.”

Motherwell have now gone 15 games without a win and remain five points ahead of bottom side Livingston.

Boss Stuart Kettlewell believes his side should have had a penalty when Rangers striker Cyriel Dessers pulled Mika Biereth inside the box.

He said: “The two penalties, the one with Brodie Spencer (tackle by Ridvan Yilmaz) may have been a soft one.

“I think there is marginal contact so I am not so sure about that.

“The one that was brought to my attention was the pull on Mika Biereth’s arm at the back post. He looks favourite to get a touch on the ball.

“It is 2-0 and one goal helps us. Watching it back, I am seeing them given as penalties constantly. I think Rangers themselves have benefited from a number of things, incidents like that. my question is, are actually checking them.

“We keep getting told that they are being checked.

“I am not sure if that specific one has been checked. I would defy anyone to tell me if it has been checked then we are OK with it because I am watching every week and slight pulls on jerseys, a slight tug of the arm, results in a penalty.

“I will probably be told that there is some other obscure rule that is the reason why it wasn’t given but with the naked eye and a replay it looks as if it has to be a penalty.”

Rangers suffered another selection blow ahead of two crucial matches after Todd Cantwell was ruled out of the trip to Spain.

The former Norwich midfielder will not feature in the Europa League decider against Real Betis on Thursday because of personal reasons.

Manager Philippe Clement was already missing Ryan Jack, Tom Lawrence and Nico Raskin from his midfield through injury as Rangers chase the win they need to guarantee progress.

Clement experienced other bad news this week. Ecuador midfielder Jose Cifuentes lost his appeal against the red card he received against Dundee on Saturday, which rules him out of Sunday’s Viaplay Cup final against Aberdeen through suspension.

And striker Danilo has been ruled out for several months with the knee injury he suffered in last Wednesday’s win over Hearts.

Clement said: “Todd is not here because of personal circumstances, and he wants to keep it personal, so we respect that. It’s nothing between the club and him, or me and him, it’s just family-wise.

“There’s a really big chance (he will be available for Sunday) but it’s not guaranteed.

“I hoped Ryan would be back but it’s not the case. Danilo will be out for several months, but I don’t want to pinpoint on an exact number of months for now until is all clear.

“I was surprised with the Cifuentes decision. None of the Dundee players reacted at the time. They just continued to attack as it was a duel with a contact. It is disappointing to lose the player for two games. But I don’t have any power in that so we will focus on the guys who are available.”

Clement is also without midfielder Kieran Dowell and defenders Leon Balogun and Ridvan Yilmaz, who are not in the club’s European squad.

“It’s quite a list of players injured and not on the European list. But it’s about the guys who are here,” he said. “They are here with ambition and to prove themselves as a team.

Rangers will go through to the knockout stages regardless of the result in Seville if Sparta Prague fail to beat Aris Limassol in Cyprus. But victory for the Czechs would leave Rangers needing to beat Betis to finish in the top two, a result which would seal top spot in Group C.

The Ibrox club are assured of European football beyond Christmas with third place sealing entry to the Conference League knockout stages.

Betis are unbeaten at home in LaLiga this season and have won both of their Group C games on home territory.

Clement said: “We have a lot of respect for them but we come here with ambition. Rangers have nothing to lose. We are in Europe next year but we want to make the next step. This may be the biggest challenge until now and we go all out for it.

“Real Betis is a different style than what we have faced. Real Madrid didn’t win here which shows how big a test it is but I feel something special in the group. I can see a really good dynamic growing in the dressing room. Everyone stays confident even after going behind.

“I see several players becoming better and better, we need to continue that story against a really good opponent.”

Meanwhile, Alex Rae has been confirmed as first-team coach on an ongoing basis after returning to Ibrox when Steven Davis took caretaker charge and staying on under Clement and assistant Stephan van der Heyden.

The former Gers midfielder told the club’s official website: “Everyone knows how much this club means to me and I am determined to help the gaffer and Stephan bring silverware back to Rangers.

“We are still in four competitions and we have a lot to look forward to this season.”

Rangers midfielder Jose Cifuentes will miss the Viaplay Cup final after losing his appeal against the red card shown to the Ecuadorian during Saturday’s victory over Dundee.

The 24-year-old was initially booked by referee Kevin Clancy after catching Amadou Bakayoko late with his studs after the Dundee forward slid in to win the ball midway through the Gers’ 3-1 win. But he was then sent off following a VAR review.

A fast-track tribunal has upheld Clancy’s final decision and Cifuentes will start a two-match domestic ban when Rangers meet Aberdeen in Sunday’s Hampden clash.

The Ibrox club have also been missing the injured Tom Lawrence, Nico Raskin and Ryan Jack from their midfield in recent games.

Philippe Clement railed against the notion that his side could be extra motivated by the prospect of winning a trophy ahead of their Viaplay Cup semi-final against Hearts.

The Light Blues have not won the competition since March 2011 and if they get past the Jambos at Hampden Park on Sunday they will face either Aberdeen or Hibernian in the December final, where the first piece of silverware of the season will be up for grabs.

Clement, unbeaten in three games since taking over as boss from Michael Beale last month, had no time for the idea that his players will have additional hunger when they come up against a side that, coincidentally, they beat 2-1 in the cinch Premiership at Ibrox last weekend.

“I hate this ‘extra motivation’,” said the Belgian. “I want that they are motivated for everything. So, if I think, ‘oh, now they are motivated for the semi-final because we can win a cup’, it’s totally the wrong message.

“They need to be motivated every day, every game to show the best of themselves.

“A football career is so short for them, it goes so fast that they need to be motivated to take the best out if every day, they have the best life in the world and that’s what I want to see from my players. And then the other things follow.”

Clement revealed that defender Ben Davies remains a doubt with a “small problem” after missing the 5-0 win at Dundee in midweek and “there is a chance but no guarantee” that attacker Tom Lawrence will return, while John Souttar, Nico Raskin, Rabbi Matondo and Kemar Roofe remain out.

He also repeated his message to the Rangers fans to leave the “dangerous” pyrotechnics at home in future.

The match at Dundee on Wednesday night was delayed by 45 minutes after the Rangers team bus was held up in traffic and then suspended for 18 minutes after Gers supporters let off a large number of flares that triggered fire alarms under the stand.

The Scottish Professional Football League will liaise with police over the “very concerning” pyrotechnic display and the former Genk, Club Brugge and Monaco boss reiterated his thoughts on the matter.

He said: “I was clear what I said after the game but I will repeat it a last time.

“I loved when we came outside for the warm-up in Dundee, you see a lot of Rangers supporters, a lot of atmosphere, songs, chants, support for the team.

“It gives the team energy. The pyro thing we don’t need. It doesn’t give something extra. It is dangerous. So if they give all the other things I will be a very satisfied manager.

“It is good that there is rules because it is such a dangerous thing. I have seen it a lot in the past but it is good that there are strict rules because we need to avoid danger for people.”

Tom Lawrence admits Rangers players were wounded by their defeat to Celtic but are determined to get back on track immediately.

The Light Blues received stinging criticism from their own supporters at the end of the 1-0 home defeat to their Old Firm rivals just before the international break, which left them four points behind Brendan Rodgers’ side with boss Michael Beale under pressure.

Ahead of the trip to St Johnstone on Saturday, attacker Lawrence, recently back after a year’s absence due to a knee injury, said: “Everyone was disappointed.

“The whole changing room was really down after the game, there were a few honest conversations.

“We know what it means to the fans. It is always difficult. We know how big those games are.

“It hurts us, it hurts the fans, it hurts everyone to do with the club.

“We know if we don’t get a result in that game it is going to hurt everybody.

“We have to have honest conversations with ourselves in the changing room and that is what we have done. It is the whole group, as a collective.

“I am not going to go into the individuals. But, like I say, it has been spoken about and all we can do is look forward to the next game and deliver in that game.”

Leon Balogun and Kieran Dowell have missed out on Rangers’ Europa League squad.

Kemar Roofe and Tom Lawrence are included after missing out on the squad for the Champions League qualifiers, as they closed in on their comebacks from long-term injury lay-offs.

Dowell has made six appearances since his summer move from Norwich, including three in the Champions League. He has missed recent matches with a minor knee injury.

https://x.com/RangersFC/status/1701584504068976861?s=20

Balogun has played twice since returning to Ibrox in the summer following a season with QPR.

Scott Wright is in the squad while Rangers confirmed the likes of Leon King and Adam Devine would be included on the list of young players who can feature outside the 25-man squad.

Rangers open their group campaign at home to Real Betis on September 21 and also take on Aris Limassol and Sparta Prague.