Aston Villa's punishment for not finishing in the top two of their UEFA Cup group was a tricky tie with in-form CSKA Moscow following the draw for the last 32 in Nyon today.
Boss Martin O'Neill has said he did not mind which side his team would draw in the knockout stages, but their hopes of progression will be tested fully by a CSKA side who won this competition in 2005 and who were the only team in the group phase to win all four of their matches.
There is the possibility of an all-English tie in the last 16 between Villa and Tottenham, who were also handed a tough tie against Ukraine side Shakhtar Donetsk.
Shakhtar dropped into the competition after finishing third in their Champions League group, with Manchester City to play Danish side FC Copenhagen.
The last 32 ties will be played on February 18 and 19 with the return legs on February 26, with the final of the tournament to be played at Fenerbahce's Sukru Saracoglu Stadium in Istanbul on May 20.