Manchester City and Manchester United will both face difficult matches in the last 32 of the UEFA Europa League after Roberto Mancini's side drew holders FC Porto and their neighbours were paired with fellow UEFA Champions League dropouts Ajax.
The Premier League pair were among the biggest names to be edged out of the Champions League group stages, both finishing third and being parachuted into today's draw in Nyon.
While many expected the demotion to Europe's second tier would be a blow to the pair's prestige, both fixtures would not be out of place in the Champions League knockout phase.
Porto, who secured the trophy last year under the guidance of now Chelsea manager Andre Villas-Boas, host City in the first leg before a return fixture at the Etihad Stadium, while United will play in the Amsterdam ArenA first.
City and Ajax both found themselves in the Europa League draw after being edged out of hard groups. City finished behind Bayern Munich and Napoli, while the Eredivisie side narrowly missed out to Lyon and Real Madrid.
Both United and Porto were bettered by less fancied opposition, with Sir Alex Ferguson's side third behind Basel and Benfica, and the Portuguese club edged by APOEL Nicosia and Zenit St. Petersburg.
Another of the big-name Champions League fallers, La Liga side Valencia, will face Stoke City, with the first leg at the Britannia Stadium.
The draw for the last 16 followed immediately on, with either United or Ajax facing a clash with Lokomotiv Moscow or Athletic Bilbao, while the winner of City's clash with Porto will go on to play either Legia Warsaw or Sporting CP. Valencia or Stoke have been slated for a fixture with one of Trabzonspor or PSV Eindhoven.
City pleased with Porto
Reflecting on City's Porto meeting, football administration officer Brian Marwood told Sky Sports News: "It's amazing, we've gone from the hardest group in the Champions League to getting the holders of the Europa League. It's a big game and we'll be looking forward to it.
"One thing we haven't had to endure is going through the early rounds where you play a lot of games. Porto are attractive opposition and the current champions. They are games we are looking forward to and are excited about."
United manager Ferguson welcomed the meeting with Ajax. He said: "I have never played them before in competitive football in my managerial career. They are a good team and we are looking forward to it."
Defender Chris Smalling added: "[Exiting the Champions League] was a massive disappoinment, but then you look at the calibre of teams that are in there [Europa League].
"We have drawn Ajax, they have a lot of history. That will be a good test. If you are in there, a lot of the teams will be kicking on. Whoever wins the competition will be a good team."
Round of 32
FC Porto v Manchester City
Ajax v Manchester United
Lokomotiv Moscow v Athletic Bilbao
Salzburg v Metalist Kharkiv
Stoke City v Valencia
Rubin Kazan v Olympiacos
AZ Alkmaar v Anderlecht
Lazio v Atletico Madrid
Steaua Bucharest v FC Twente
Viktoria Plzen v Schalke
Wisla Krakow v Standard Liege
SC Braga v Besiktas
Udinese v PAOK Salonika
Trabzonspor v PSV Eindhoven
Hannover v Club Brugge
Legia Warsaw v Sporting CP
Round of 16
Salzburg/Metalist v Rubin/Olympiacos
Legia/Sporting v Porto/Manchester City
Steaua/Twente v Plzen/Schalke
Wisla/Standard v Hannover/Club Brugge
Stoke/Valencia v Trabzonspor/PSV
AZ/Anderlecht v Udinese/PAOK
Lazio/Atletico v Braga/Besiktas
Ajax/Manchester United v Lokomotiv/Athletic