Arsenal will play seven-time European champions AC Milan in the Europa League last 16.
The Gunners will travel to Italy for the first leg on 8 March, with the return match a week later.
Milan, who are seventh in Serie A, beat Bulgarian club Ludogorets Razgrad 4-0 on aggregate in the previous round.
Arsene Wenger’s Gunners beat Swedish minnows Ostersunds FK 4-2 on aggregate in the last 32, despite a “complacent” performance in Thursday’s second leg.
Wenger said his team “had no ideas with the ball” after they lost 2-1 at home to a side only founded in 1996, who have risen from Sweden’s fourth tier in seven years under English manager Graham Potter.
Russian club Zenit St Petersburg, who knocked out Scottish champions Celtic, play RB Leipzig of Germany.
In each of their previous seven seasons in Europe, Arsenal were knocked out of the Champions League at the last-16 stage.
One of those exits – in 2012 – was in their most recent meeting with Milan.The Gunners lost the first leg at the San Siro 4-0 before winning 3-0 at home.
Despite their European pedigree, the Italian giants have never won the Europa League – nor its predecessor, the Uefa Cup.
Led by their former midfielder Gennaro Gattuso, they are 25 points behind Serie A leaders Napoli, despite having spent around £200m on signings in the summer transfer window.
Europa League last-16 draw in full:
Lazio v Dynamo Kiev
RB Leipzig v Zenit St Petersburg
Atletico Madrid v Lokomotiv Moscow
CSKA Moscow v Lyon
Marseille v Athletic Bilbao
Sporting Lisbon v Viktoria Plzen
Borussia Dortmund v Red Bull Salzburg
AC Milan v Arsenal