Manchester United will take on Real Sociedad while Rangers will face Jose Mourinho's Fenerbahce in the last 16 of this season’s Europa League.
United’s reward for automatic qualification is a showdown with Spain's Sociedad, currently 11th in LaLiga, who put five past Midtjylland to add to their 2-1 win in the away leg as they progressed 7-3 on aggregate.
United, who lifted the trophy in 2017, last met Sociedad in the same competition in 2022-23 when both matches ended 1-0 to the away side.
Premier League counterparts Tottenham will lock horns with AZ Alkmaar for the second time this season, with Republic of Ireland attacker Troy Parrott getting another chance to haunt his old club.
Parrott has been a big hit in the Eredivisie since moving to AZ from Spurs last summer.
The Dutchmen lost 1-0 in North London during the group stage in October when Richarlison’s penalty proved decisive on a night when the visitors had defender David Moller Wolfe sent off with five minutes remaining.
The Scottish club, who finished eighth in the group phase table, have been drawn against the Turkish Super Lig outfit after their 5-2 aggregate victory over Anderlecht, which was secured by a 2-2 draw in the second leg of their play-off in Belgium on Thursday evening.
Rangers and Fenerbahce currently lie second in their respective leagues' with Philippe Clement's men 13 points adrift of leaders Celtic and Mourinho’s charges six shy of Galatasaray.
For United and Spurs, the competition perhaps represents their best chance of winning a trophy this season.
Spurs are 12th in the Premier League after last weekend’s 1-0 win over Ruben Amorim’s side, who sit 15th.
The ties will take place on March 6 and 13.
Should Rangers progress, they will face either Roma or Athletic Bilbao in the quarter-final, while United would line up against FCSB or Lyon and Spurs Ajax or Eintracht Frankfurt.
Chelsea will face Danish Superliga leaders Copenhagen for a place in the quarter-finals of the Conference League.
Enzo Maresca's side had a 100% group-phase record, including a 5-1 win over Shamrock Rovers, which allowed them to top the table with 18 points.
Copenhagen made it to the knockout stage the hard way, losing the home leg of their play-off against Germany’s Heidenheim 2-1 before securing a nail-biting 3-1 extra-time victory in the return to secure their passage.
The sides met in the European Cup Winners’ Cup in 1998 with the Blues going through 2-1 on aggregate after Brian Laudrup scored the decisive goal in Denmark.
However, they last went head-to-head in the last 16 of the Champions League in 2011 when Nicolas Anelka’s double in the away leg handed the Blues a 2-0 advantage to take to Stamford Bridge, where a 0-0 draw pitched them into last-eight battle, ultimately unsuccessfully, with Manchester United, who would go on to lose to Barcelona in the final at Wembley.
Norwegian side Molde, who beat Shamrock Rovers on penalties last night, face Poland's Legia Warsaw.
The ties will take place on March 6 and 13.
