Not since Graeme Le Saux and David Batty traded punches 16 years ago has English football been without a representative in the Champions League quarter-finals but that prospect loomed yesterday after the surviving clubs, Arsenal and Chelsea, were handed demanding second-round ties against Italian opposition.
Arsenal must play Serie A champions and seven-times European Cup winners Milan; Chelsea face Napoli, conquerors of Manchester City in the group stages.
Despite their opponents' pedigree, both English sides should start as narrow favourites, but the draw was nevertheless scant reward for topping their qualifying groups. The London clubs could only look on enviously as Lyon, who only squeezed through because Dinamo Zagreb collapsed in the last group-stage round, drew rank outsiders Apoel Nicosia.
Holders Barcelona expect to progress against Michael Ballack's Bayer Leverkusen, to judge from the verdict of president Sandro Rosell ("We got Bayer, well, perfect"). So will Bayern Munich, who host the final, even if opponents Basle unexpectedly put Manchester United out. But Jose Mourinho's Real Madrid have a tricky tie against CSKA Moscow, during which they are likely to have to play in Moscow on a plastic pitch in sub-zero temperatures.
It was in Moscow that Le Saux and Batty came to blows as Blackburn Rovers departed the Champions League in ignominy. Back then only League champions were allowed entry. The competition has much greater depth now (Nantes and Panathinaikos made the semi-finals in 1995-96) and Arsenal and Chelsea were sanguine about their fates.
"I think we have one of the most difficult draws, but whichever team you get in the last 16 will be difficult," Andre Villas-Boas said. He added: "They are a side that works collectively very well and [Napoli coach] Walter Mazzarri organises his teams very well."
Napoli's swift counter-attacking expertise will present another test of Villas-Boas's determination to turn Chelsea into an expansive attacking team. The Portuguese was happy to have the second leg at home. "It is a big advantage," he said. "It can stimulate your fans to create the right environment to help you to go through. The last two matches at Stamford Bridge, against Valencia and Man City, saw a totally different stadium environment."
Chelsea look likely to have to meet the challenge of dealing with Edinson Cavani after the Uruguayan pledged his immediate future to Napoli following speculation linking him with moves to England and Spain.
"I like English football a lot – there are teams that are both strong and exciting," Cavani said, "and there's lots of space in the Spanish game which would suit me, but my future is with Napoli. I have no doubts about that."
Arsenal director David Miles admitted of Milan: "There are other teams we would have preferred," but added that having lost to Barcelona in the last two seasons any opponent was an improvement. Manager Arsène Wenger said: "It is a difficult draw, but an exciting one, they could say exactly the same thing. It is a 50-50." Arsenal's injury list should have been trimmed by then with Jack Wilshere a possible inclusion.
Arsenal lost the Super Cup in a foggy San Siro in 1995 but beat Milan four seasons ago. Milan went out to Tottenham last year when their ageing team was exposed and while there has been some new blood, Milan have not convinced in Europe this year, losing in Barcelona and being held away to Bate Borisov, of Belarus, and Viktoria Plzen, of Czech Republic.
By February, Milan could have an attack to give coach Max Allegri dreams and nightmares with the club hoping to add Carlos Tevez to Zlatan Ibrahimovic and Robinho. Owner Silvio Berlusconi said he hoped the Argentine would put glory ahead of money. "At Milan he could gain international prestige, which would not happen at Paris Saint-Germain," he said.