Pep Guardiola’s problems mounted as Manchester City were held to a 1-1 draw by Liverpool, while Tottenham beat Southampton 2-1 to keep in touch with runaway leaders Chelsea on Sunday.

Manchester United extended their unbeaten league run to 18 games as a 3-1 victory at relegation-threatened Middlesbrough took them up to fifth place.

Guardiola was criticised after his side crashed out of the Champions League against Monaco in midweek and the Spaniard suffered another blow as City’s slender hopes of catching Premier League leaders Chelsea were effectively ended at Eastlands.

City defender Gael Clichy gifted Liverpool a 51st minute penalty when he was beaten to a high ball by Roberto Firmino and compounded his mistake by fouling the Liverpool forward in the area.

Former City star James Milner, jeered by his old club’s fans, stepped up to hammer the spot-kick past Willy Caballero.

Guardiola’s side equalised in the 69th minute when Kevin De Bruyne whipped in an excellent cross and Sergio Aguero slotted home for his 25th goal of the season.

But, despite chances aplenty in the closing stages of a thrilling clash, there was no winner for third placed City, who are now 12 points behind Chelsea and stay just one point ahead of fourth placed Liverpool.

At White Hart Lane, Tottenham proved they can thrive without leading scorer Harry Kane and closed the gap on Chelsea to 10 points.

Kane was ruled out for up to six weeks after suffering an ankle injury in last weekend’s FA cup quarterfinal victory over Millwall.

But Mauricio Pochettino’s men still looked formidable as Danish winger Christian Eriksen drilled home with a fine finish in the 14th minute.

Dele Alli won a 33rd minute penalty after being fouled by Southampton’s Steven Davis and the Tottenham midfielder picked himself up to convert the spot-kick.

Seven minutes after the interval, Ryan Bertrand’s left wing cross should have been cleared by Spurs centre-back Toby Alderweireld, but James Ward-Prowse finished well at the far post.

SUPER HAPPY

With 10 games remaining, Tottenham’s chances of overhauling Chelsea’s lead are slim, but victory strengthened their position in the fight to guarantee a top four finish by extending the gap to fifth place to seven points.

“It was difficult. In the end we were better and deserved to win,” Pochettino said.

“It is another victory, we keep our position in second and we are happy.”

At the Riverside Stadium, Marouane Fellaini scored his first league goal for 15 months to put United ahead after 30 minutes.

Jesse Lingard added a stunning second in the 62nd minute before Rudy Gestede got one back for Middlesbrough in the 77th minute.

Antonio Valencia grabbed a stoppage-time third after an embarrassing mistake by former United keeper Victor Valdes.

United’s latest victory made them the first club to record 600 Premier League wins and put them within four points of the top four in the race to qualify for the Champions League.

“I am super happy. The attitude of the boys was magnificent. I think I made them feel important and trusted,” United boss Jose Mourinho said.

“The spirit is fantastic. We have two doors still open for Champions League football.”

Middlesbrough remain second-bottom, five points adrift of safety after an 11th league game without victory as caretaker manager Steve Agnew tasted defeat in his first match following the departure of Aitor Karanka.

Gestede initially appeared to bite defender Eric Bailly in a stoppage time melee on the edge of the visitors’ area.

Replays showed there was no contact as the pair engaged in an angry clinch, but punches appeared to be thrown afterwards in the players’ tunnel as both sides left the pitch. (© AFP)

•Photo shows embattled Manchester City Manager Pep Guardiola