Europa League draws in full
Roy Hodgson's Reds face Sparta Prague of Czech Republic, while Roberto Mancini will takes his Blues to Greece to take on Aris, who knocked holders Atletico Madrid out of the competition on Thursday.
Sevilla and Porto, winners between them of three of the five UEFA Cup finals between 2003 and 2007, were drawn to meet each other in the last 32 of the Europa League on Friday.
Sevilla won the UEFA Cup, the forerunner of the Europa League, in 2006 and 2007 while Jose Mourinho launched his career by guiding Porto to victory in 2003, coincidentally winning the final in Seville.
Lech Poznan, who qualified at the expense of Juventus from the same group as Manchester City, will face Braga, one of eight teams parachuted in from the Champions League after failing to progress in Europe's top club competition - something many observers feel devalues the Europa League.
Anderlecht and Ajax Amsterdam, both major forces in European football in the 1970s and 1980s, will meet in a tie which is bound to have their fans longing for the old days.
Anderlecht twice won the extinct Cup Winners Cup and the UEFA Cup once while Ajax won the European Cup three times in a row the 1970s and once again in 1995, plus the Cup Winners Cup and UEFA Cup once each.
Neither team can now be considered among Europe's elite, with Ajax outclassed by Real Madrid as they were knocked out in the group stage in their first Champions League appearance for five seasons.
Two of the four Russian teams were draw against Swiss sides.
Zenit St Petersburg, UEFA Cup winners in 2008, will face Young Boys while Spartak Moscow were pitted against FC Basel.
Rubin Kazan play Dutch champions Twente Enschede and CSKA Moscow - winners in 2005 - play PAOK, with the winners of that tie facing either Porto or Sevilla.
VFB Stuttgart, who cruised through their group but are one off the bottom of the Bundesliga, will face Benfica.
Napoli v Villarreal RANGERS v Sporting Sparta Prague LIVERPOOL Anderlecht v Ajax Lech Poznan v Braga Besiktas v Dynamo Kiev Basel v Spartak Moscow Young Boys v Zenit Aris v MANCHESTER CITY* First leg February 15 PAOK v CSKA Moscow** Second leg February 22 Sevilla v Porto** Second leg February 22 Rubin Kazan v Twente Lille v PSV Benfica v Stuttgart BATE v PSG Metalist v Bayer Leverkusen
Ties will take place on February 17 and 24, unless stated otherwise above.
Benfica/Stuttgart v BATE/PSG Besiktas/Dynamo Kiev v Aris/MANCHESTER CITY Rubin Kazan/Twente Young Boys/Zenit PAOK/CSKA Moscow v Sevilla/Porto Lille/PSV v RANGERS/Sporting Metalist/Bayer Leverkusen v Napoli/Villarreal Anderlecht/Ajax v Basel/Spartak Moscow Sparta Prague/LIVERPOOL v LechPoznan/Braga
Ties will take place March 10 and 17. The draw for the final stages is scheduled for March 18. The final will be played in Dublin on May 18.