Wayne Rooney missed a penalty as Manchester United crashed out of the Capital One Cup at the hands of Middlesbrough at Old Trafford.
Championship promotion-chasers Boro had a goal disallowed when Kike hit the post and Daley Blind put the rebound in the own net, with an offside flag curtailing their celebrations.
Stewart Downing also forced a stunning save from Sergio Romero while Jesse Lingard hit a post for United but the 90 minutes finished goalless.
Neither side could break the deadlock in extra time with Anthony Martial and Marouane Fellaini missing close-range headers at the death for United.
Rooney saw United’s first penalty saved by Tomas Mejias, Michael Carrick blazed over and Mejias then blocked Ashley Young’s effort as Boro triumphed 3-1 on spot-kicks.
Jurgen Klopp broke his win duck at the fourth attempt as Liverpool beat Bournemouth 1-0.
Nathaniel Clyne grabbed the goal as Klopp, who has overseen three draws since taking over as Anfield boss, finally celebrated a victory.
Right-back Clyne grabbed the goal in the 17th minute when a cute backheel by youngster Joao Carlos Teixeira was not properly cleared.
The ball fell kindly to the England international, who had continued his run to the far post to fire home his first Reds goal.
Manchester City have been moved into 11/10 by Sky Bet to win the Capital One Cup following Wednesday night’s drama and draw. Liverpool come next in the market at 5/1 with Everton and Southampton both at 6s. Middlesbrough are 16/1 to lift the trophy following their heorics at Old Trafford. Click here for all the latest odds.
Kevin De Bruyne’s sixth goal in nine appearances helped Manchester City sweep past Crystal Palace 5-1.
Wilfried Bony opened the scoring in the 22nd minute when he headed in Aleksandar Kolarov’s cross.
De Bruyne doubled the lead on the stroke of half-time when he tucked in an inviting cross from Kelechi Iheanacho.
And De Bruyne returned the favour on the hour mark when he teed up Iheanacho for his second City goal – both of which have come against Palace.
Yaya Toure made it four 15 minutes from time with a penalty for his first home goal since New Year’s Day, Damien Delaney pulled one back but youngster Manu Garcia promptly tucked away the fifth.
Maya Yoshida and Graziano Pelle were on target as Southampton sank managerless Aston Villa 2-1 at St Mary’s.
In the 51st minute Japan striker Yoshida linked up with Gaston Ramirez, making a rare appearance in the Saints’ starting XI, before firing home off the inside of Brad Guzan’s post.
And as Villa chased an equaliser they were caught out on the break as Pelle crashed in a superb volley for his eighth goal of the season.
Scott Sinclair pulled one back from the spot for Villa deep into stoppage time but there was barely time to kick-off.
Capital One Cup Quarter-Final Draw
Middlesbrough v Everton
Southampton v Liverpool
Stoke City v Sheffield Wednesday
Manchester City v Hull City
Ties to be played December 1 & 2