Liverpool and Arsenal have paid the price for finishing second in the their Champions League groups with draws Inter Milan and AC Milan in the first knockout round.
The Gunners will meet the holders AC Milan in February, while Rafa Benitez's Liverpool side go up against the reigning Serie A champions and current league leaders Inter Milan.
Sir Alex Ferguson's Manchester United have a tough match against the dangerous French champions Lyon while Scottish representatives Celtic are facing up to two matches against Spanish giants Barcelona.
Chelsea were drawn against Olympiacos of Greece and the other big tie in the last 16 pits mighty Real Madrid against Francesco Totti and Roma.
Schalke 04 of Germany take on 2004 winners FC Porto and Sevilla face Turkish side Fenerbahce.