Premier League sides learned their fate in the UEFA Europa League, and not one of them were handed an easy path to the Round of 16.
Manchester United drew Club Brugge, who transferred from the Champions League after a third place finish. The sides met in UCL qualifying back in 2015, the Red Devils cruising past the Belgians.
[ MORE: Champions League draw ]
Arsenal tangles with stingy Greek side Olympiacos, having met in four Champions League group stages between 2009-15.
Wolves draw a side its never faced: La Liga mainstay Espanyol.
The notable matches don’t stop there.
American coach Jesse Marsch will lead Red Bull Salzburg against the Bundesliga’s Eintracht Frankfurt.
Old Firm rivals Celtic and Rangers both learned their fates, the Bhoys will meet Danish powers Copenhagen and Steven Gerrard’s Rangers clash with Braga.
The Round of 32 matches will be staged Feb. 20 and 27.
Europa League Round of 32
Wolves v. Espanyol
Sporting Lisbon v. Istanbul Basaksehir
Getafe v. Ajax
Bayer Leverkusen v. Porto
Copenhagen v. Celtic
APOEL Nicosia v. Basel
CFR Cluj v. Sevilla
Olympiacos v. Arsenal
AZ Alkmaar v. LASK
Club Brugge v. Manchester United
Ludogorets Razgrad v. Inter Milan
Eintracht Frankfurt v. Red Bull Salzburg
Shakhtar Donetsk v. Benfica
Wolfsburg v. Malmo
Roma v. Gent
Rangers v. Braga