Newcastle, competing in the knockout stages of European competition for the first time, will take on Qarabag over two legs. The Magpies will travel roughly 5,000 miles for the first leg, scheduled for February 17 or 18, before hosting the return leg at St James' Park on February 24 or 25 due to their seeded status.

The tie further intensifies Newcastle's packed February schedule. Eddie Howe's side are also set to face Manchester City on February 21 and Everton on February 28 in the Premier League. While Qarabag suffered a heavy 6-0 defeat to Liverpool earlier in the competition, they showed resilience by holding Chelsea to a 2-2 draw earlier in the league phase. Should Newcastle progress, they will face either Chelsea or Barcelona in the last 16.

Elsewhere, one of the most compelling ties will see Real Madrid face Benfica, setting up another chapter between Mourinho and his former club. Madrid dropped into the play-offs after a chaotic 4-2 defeat to Benfica in their final league phase fixture. Reduced to nine men, the Spanish giants conceded a dramatic late goal when Benfica goalkeeper Anatoliy Trubin scored deep into stoppage time.

The result saw Alvaro Arbeloa's side slip to ninth in the standings, missing automatic qualification for the round of 16 and forcing them into the play-off round. Benfica, who have won three of the last four European meetings between the two clubs - including the 1962 European Cup final - will host the first leg before travelling to the Santiago Bernabeu.

Defending champions Paris Saint-Germain were also forced into the play-offs after dropping points late in the league phase. The French giants will face domestic rivals Monaco in an all-Ligue 1 showdown as they attempt to keep their title defence alive.

Several other heavyweight clubs also face tricky ties. Juventus have been drawn against Galatasaray, while last season's runners-up Inter Milan will take on Norwegian champions Bodø/Glimt, who notably beat Manchester City during the league phase.

Atletico Madrid will meet Club Brugge, while German sides Borussia Dortmund and Bayer Leverkusen face Atalanta and Olympiacos respectively.

The winners of the play-off ties will secure places in the round of 16, with that draw set to take place after the play-off round concludes on February 27.

Newcastle handed long trip as Mourinho set for Madrid reunion in Champions League play-offs