CSKA Moscow were drawn against Spanish giants Real Madrid in the last 16 of the Champions League on Friday, while Zenit St. Petersburg face less daunting opponents in Portuguese side Benfica.
CSKA, in the knockout stages for only the second time, have never played the nine-time champions Real Madrid, who were stopped in last season's seimfinal by eventual winners Barcelona.
Last-16 debutants Zenit and Benfica, the 2006 quarterfinalists, also clash for the first time in the competition.
As the runners-up in their respective groups, CSKA and Zenit will have the disadvantage of playing their first legs at home, in mid-February, and their second legs away, in early March, although the cold Russian winter may be a leveller.
The draw at UEFA headquarters in Nyon, Switzerland, gave Italian tests to the two English representatives by pitting Chelsea against Napoli and Arsenal with AC Milan. Elsewhere, Barcelona play 2002 finalists Bayer Leverkusen and Inter Milan, who knocked out CSKA in the 2010 quaterfinals, play Marseille. The tournament's surprise package, APOEL Nicosia, face Lyon.