Liverpool and Arsenal have paid the price for finishing second in the their respective Champions League groups with respective draws against Inter Milan and AC Milan in the first knockout round.
The draw, held in Nyon this morning, also left Celtic facing up to two matches against Spanish giants Barcelona, while Chelsea have it slightly easier after being drawn with Olympiacos.
The other British side in the last 16 of the competition, Sir Alex Ferguson's Manchester United, will play French side Lyon.
Liverpool, whose form in the knockout phase of the competition has been impressive under Rafael Benitez, finished strongly in Group A with a 4-0 win at Marseille but they could only finish as runners-up after a slow start to their campaign.
That means they face the current Serie A leaders, with the first leg at Anfield, for the first time in the Champions League.
The sides last met competitively in the European Cup semi-final in 1965, a two-legged contest which Inter won on aggregate.
Gordon Strachan's Celtic are more familiar with their opponents, having played Barca four times in 2004 - twice in the UEFA Cup and twice in the Champions League.
The Hoops lost just one of those matches, beating them 1-0 at home in the former competition.
The last time United met their French opponents was in 2004, when they drew at Lyon in the group stages before beating them 2-1 at Old Trafford thanks to Ruud van Nistelrooy's winner.
Arsenal have not been pitted against reigning champions AC Milan since the Italians beat them 2-0 in the 1995 European Super Cup final but, having made the final in 2006, they will be hoping to avoid a repeat of that result.
Chelsea boss Avram Grant, meanwhile, will be positive about his chances of providing Roman Abramovich with the continental success his predecessor Jose Mourinho could not after being drawn with the Greek side.
The Blues, who play the first leg away before hosting the decisive clash at Stamford Bridge, will be favourite to progress in what is the first meeting between the sides.
Elsewhere in the draw German side Schalke meet Porto, Roma play Real Madrid and Fenerbahce tackle Sevilla.