Manchester United drew 1-1 away to Real Sociedad in the first leg of their Europa League last-16 tie on Thursday, while Tottenham suffered a 1-0 loss at Dutch side AZ Alkmaar.

Manchester United were drawn Friday to play Real Sociedad of Spain in the last 16 of this season's Europa League, while Rangers will take on Jose Mourinho's Fenerbahce, and Tottenham Hotspur face AZ Alkmaar.

Tottenham won the battle of the Premier League's underachievers 1-0 on Sunday to inflict another dismal result on Manchester United boss Ruben Amorim.

Liverpool suffered a stunning FA Cup exit on Sunday in a 1-0 defeat to Championship strugglers Plymouth

Liverpool overturned a first leg deficit to reach the League Cup final with a 4-0 win over Tottenham on Thursday

Former Barcelona midfielder Nico Gonzalez, 23, arrives for a reported fee of 60 million euros (50 million euros, $62 million).

Manchester United slumped to another meek home defeat as Crystal Palace won 2-0 at Old Trafford on Sunday, while Tottenham eased the pressure on Ange Postecoglou by beating Brentford 2-0.

Manchester United, unbeaten in eight games in the tournament, finished in third place and Tottenham came fourth, ensuring the Premier League clubs both avoided the Europa League play-off round.

Manchester United and Tottenham are among the sides aiming to ensure direct passage to the Europa League last 16 in Thursday's league phase finale with nine places in the knockout stages up for grabs

Leicester pushed Tottenham boss Ange Postecoglou closer to the exit door with a 2-1 win that extended Spurs' dismal run

Son Heung-min helped Tottenham gain some respite from their Premier League woes on Thursday with a double in a 3-2 Europa League win at Hoffenheim

Manchester United slumped to a 3-1 defeat at home to Brighton as Old Trafford remembered the legendary Denis Law on Sunday, while Tottenham's troubles also persist after they lost 3-2 at Everton.

Arsenal came back from 0-1 down to win 2-1 against Tottenham, closing the gap to Liverpool to four points for the time being.

A controversial moment wrapped up the first leg of the Carabao Cup tie between Tottenham and Liverpool.

Lucas Bergvall condemned Liverpool to only their second defeat this season as the teenager's late strike earned Tottenham a controversial 1-0 win in the League Cup semi-final first leg.

Tottenham vs Liverpool LIVE Streaming, Carabao Cup LIVE Telecast EFL Cup: When And Where To Watch

Erling Haaland scored twice as Manchester City pummelled West Ham 4-1 in the Premier League on Saturday while in-form Newcastle inflicted another painful defeat on Ange Postecoglou's struggling Tottenham.

Thomas Tuchel will mark the official start of his England reign by watching Tottenham play Newcastle in the Premier League on Saturday.