Of the sides remaining, Chelsea, Tottenham Hotspur and Newcastle United were no doubt hoping to avoid each other, and also a lengthy trip to Russia to face Rubin Kazan. That left, Basel, Benfica, Lazio and Fenerbahce, with the Italian side the only unbeaten team left in the tournament.
Chelsea were the first of three out of the hat, drawing Rubin Kazan, meaning they would face the slog to Russia in amongst their already jam-packed schedule. Rubin might not be the strongest side on paper, but their win over Levante was impressive, and Chelsea will not be delighted to have picked them out of the hat. Chelsea will play the first leg at Stamford Bridge, and will perhaps hope to put the tie out of sight and leave a few key men at home when they go to Russia.
Tottenham Hotspur were next, drawing Basel. Spurs will be pleased to have been paired with the relatively nearby Swiss team, and once again will play their first leg at home, an advantage that they have used to its full extent so far. Basel will be no pushovers though, having knocked out Zenit in the last round. Spurs will always be happy to see Chelsea travelling to Russia, with the two teams fighting it out for a Champions League place in the Premiership and currently scheduled to play each other in the league shortly after the away legs of their ties.
Fenerbahce then drew Lazio, leaving Newcastle paired with Benfica in perhaps what is the standout tie of the round, with Alan Pardew's side heading to Portugal for the first leg. Benfica came through a tight tie with Bordeaux in the last round, and Newcastle will have to be especially wary of the Paraguayan striker Oscar Cardozo. Newcastle played another Portuguese side at this stage in 2004/05, being knocked out by Sporting.
The first round of matches will take place on the 4th of April, with the return legs a week later on the 11th.
The draw in full: Chelsea vs Rubin Kazan, Tottenham Hotspur vs Basel, Fenerbahce vs Lazio and Benfica vs Newcastle United.