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
“To a man we were very good … by much the better side,” Gerrard said. “But unfortunately that’s not what gets you a trophy.”
But Celtic goalkeeper Fraser Forster stopped Alfredo Morelos’ penalty, three minutes after goal scorer Christopher Jullien was offside on the lone goal of the game.
Scotland doesn’t yet use VAR, and Gerrard doesn’t love VAR but he likes it more than he likes Scottish officials.
“There were three Celtic players standing in offside positions but unfortunately we play in a country where there is no VAR,” he said, via the BBC. “I’d be a liar if I said I was 100% in favour of it, but the one thing I do know is that officials up here need support.”
Now he has the task of getting his men to rebound ahead of its biggest non-derby in ages, as Rangers need at least a draw against Young Boys at home on Thursday to advance to the Europa League knockout rounds
“It’s a bit raw right now… It’s up to me to pick the players up. One thing I will say is I’ll stay with these players on the evidence of today because they gave me absolutely everything. We might have to suffer a bit short-term. I need to pick them up a bit physically and mentally for Thursday which is huge but our day will come on the evidence of today.”
Gerrard has done a very good job with Rangers, who are two points back of Celtic in a two-horse race for the Scottish top flight title. Celtic has won eight-straight titles to improve their total to 50, four less than the Rangers.
At some point, Rangers supporters will be forgiven for thinking Celtic doesn’t have all the luck in Scotland.
The Bhoys, second best for most of the day, scored a 60th minute goal and then overcame a red card three minutes later to claim their 10th successive piece of Scottish silverware with a 1-0 win the Scottish League Cup.
Celtic’s Chris Jullien prodded home a free kick before 18-year-old Jeremie Frimpong was sent off, and Rangers had already controlled the proceedings before seeing a 16-5 edge in shot attempts at the final whistle.
Goalkeeper Fraser Forster, the former Saints and Newcastle man, was outstanding in the win, even stopping an Alfredo Morelos penalty as the Rangers star failed to deliver.
“It was just one of them days, it went my way today. I’m buzzing. There’s been days when it’s not gone my way, today it has. I can’t say how much it means to me. I didn’t really think about the penalty to be honest. I picked the way it went. I’ll take it.
“That’s why I came back; to play in games like this, to win silverware, to play European football.”
Wout Weghorst scored the lone goal and USMNT back John Brooks played a standout role in a clean sheet as Wolfsburg joined Gent in advancing from Group I.
Malmo 4-3 Dynamo Kyiv
The first goal came from Rasmus Bengtsson in the second minute, and the game rarely stopped delivering from that point.
Malmo led 1-0, then trailed 2-1 at the break. The hosts then took a 3-2 lead only to find themselves level with the Ukrainians in the 77th. Markus Rosenberg then did this in stoppage time, and Malmo was pleased with him.
Wolves know a point at Braga will secure their spot in the Round of 32, while Arsenal host Eintracht Frankfurt knowing a point will also see them into the knockout round. Even if Arsenal lose, they will go through if Standard Liege lose their match against Vitoria Guimaraes.
Some other eye-catching games see already qualified Celtic host Rennes, Rangers travel to Feyenoord as they aim to reach the knockout round, while Sporting Lisbon host PSV and Saint-Etienne welcome Gent in two tasty clashes.
Below is the schedule in full for the games which kick off across two windows at 12:55 p.m. ET and 3 p.m. ET.
Early games (kick off time, 12:55 p.m. ET)
Oleksandriya v. Wolfsburg
Ferencvaros v. Espanyol
Feyenoord v. Rangers
Young Boys v. Porto
Saint-Etienne v. Gent
Istanbul Basaksehir v. Roma
Braga v. Wolves
Wolfsberger v. Borussia Monchengladbach
Besiktas v. Slovan Bratislava
AZ Alkmaar v. Partizan Belgrade
CSKA Moscow v. Ludogorets Razgrad
Late games (3 p.m. ET)
Celtic v. Rennes
Lazio v. CFR Cluj
Sporting v. PSV Eindhoven
Rosenborg v. LASK
Sevilla v. Qarabag
Dudelange v. APOEL Nicosia
Malmo v. Dynamo Kiev
Arsenal v. Eintracht Frankfurt
Vitoria v. Standard Liege
Lugano v. Copenhagen