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Holders Manchester City will face FC Copenhagen in the last 16 of the Champions League.
Arsenal, the current Premier League leaders, will take on Portuguese side Porto in the first knockout round.
The ties, the first legs of which will take place over two weeks in February 2024, were confirmed after the draw at the Swiss headquarters of organiser UEFA in Nyon on Monday.
City played Copenhagen – who came through a group that included Manchester United – in the early stages last season, winning 5-0 at the Etihad Stadium and drawing 0-0 in Denmark.
Pep Guardiola’s side, who are currently in Saudi Arabia for the Club World Cup, qualified this time with a 100 per cent record in Group G.
Arsenal were also convincing winners of Group B on their return to the competition after a six-season absence.
Their opponents Porto came through as runners-up to Barcelona in Group H.
Spanish champions Barca, meanwhile, were handed a tough task against Serie A winners Napoli.
In the other ties, record 14-time winners Real Madrid were paired with RB Leipzig and their city rivals Atletico drawn against Inter Milan.
Paris St Germain will play the fourth Spanish side in the draw, Real Sociedad, with the two German teams, Bayern Munich and Borussia Dortmund, tackling Lazio and PSV respectively.
As winners of their groups, City and Arsenal will play the first legs of their ties away.
The first legs will take place on February 13, 14, 20 or 21 with the return matches on March 5, 6, 12 or 13.
The draw for the Europa League knockout play-off round, which featured the eight group runners-up plus eight teams dropping down from the Champions League, was also made.
Brighton, Liverpool, West Ham and Rangers were not involved, having all topped their groups and progressed straight through to the last 16.
Galatasaray, who edged out Manchester United to take third in their Champions League group, will face Sparta Prague, with AC Milan, who finished above Newcastle, facing Rennes. Other notable ties were Feyenoord v Roma and Shakhtar Donetsk v Marseille.
Ajax were drawn against Norwegian outfit Bodo/Glimt in one of the standout ties in the Europa Conference League knockout play-off round, with Eintracht Frankfurt facing Belgian league leaders Union Saint-Gilloise. Aston Villa did not feature in the draw having already secured their last-16 place.
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