Rangers will face Jose Mourinho's Fenerbahce in the last 16 of this season's Europa League.
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.
Manchester United's reward for automatic qualification is a showdown with Spanish side Real Sociedad, 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 Hotspur will lock horns with AZ Alkmaar for the second time this season.
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.
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.
They last met in the third qualifying round of the Champions League in 2001, when the Turks progressed courtesy of a 2-1 second leg win in Istanbul after a goalless draw in Glasgow.
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, meanwhile, face Copenhagen in the Uefa Conference League.
PA
