Liverpool, who slipped out of the Champions League and into its sister competition, face a tough draw against Besiktas in the Round of 32. The Turkish side proved stubborn opponents against Arsenal before the Gunners finally came through their qualification match for the Champions League earlier this season.
Liverpool won their last meeting with Besiktas 8-0 in the 2007-08 Champions League. Current captain Steven Gerrard scored in the game but the other goalscorers - Yossi Benayoun with a hat-trick and Peter Crouch and Ryan Babel netting twice apiece - have long since departed Anfield.
The first-leg matches will be played on February 19, with the return fixtures seven days later.
Tottenham will play Italian side Fiorentina, a team they have never faced. Fiorentina are currently eighth in the Serie A table.
Celtic also face Italian opposition having been drawn against Inter Milan and might feel confident having never lost to them. The draw marks a reunion with the opposition for the most famous match in the club's history, the 1967 European Cup final which Jock Stein's 'Lisbon Lions' won 2-1.
The final Premier League side remaining in the competition, Everton, will play Swiss side Young Boys in the first knock-out round of the Europa League. The Toffees have never played them before.
Reigning champions Sevilla were handed a tough draw against Borussia Monchengladbach who are currently fourth in the Bundesliga.
Young Boys v Everton
Torino v Athletic Bilbao
Sevilla v Borussia M'gladbach
Wolfsburg v Sporting
Ajax v Legia Warsaw
AaB v Club Brugge
Anderlecht v Dinamo Moscow
Dnipro v Olympiacos
Trabzonspor v Napoli
Guingamp v Dynamo Kiev
Villarreal v SV Red Bull Salzburg
Roma v Feyenoord
PSV v Zenit St Petersburg
Liverpool v Besiktas
Tottenham Hotspur v Fiorentina
Celtic v Inter Milan
Games will be played on 19 and 26 February.Reuse content