The UEFA Europe League announced the draw for the round of 32 on Monday, with the first leg set to be played on Feb. 19 and the second to follow on Feb. 26.
In two of the knockout stage's noteworthy matchups, Liverpool will face Turkish side Besiktas, while Tottenham will meet Italian side Fiorentina.
Liverpool and Besiktas last met in 2007, when Liverpool defeated the Turkish club 8-0 in the Champions League, a competition-record margin of victory in a match that featured a hat-trick from Yossi Benayoun.
Other fixtures include defending champion Sevilla against Bundesliga side Borussia Monchengladbach. The two clubs will meet for the first time, but together have won the championship five times.
Wolfsburg, the other team from the Bundesliga, will face Sporting, which was recently knocked out of the Champions League. Everton, featuring U.S. men's national team keeper Tim Howard, will play Swiss side BSC Young Boys.
After the conclusion of the round of 32 on Feb. 26, the round of 16 draw will take place on Feb. 27 with matches to follow on March 12 and 19. The championship will be on May 27 in Warsaw.
The full slate and kick-off times for each match can be found here.