Ever since last week, Arsene Wenger and Manuel Pellegrini must both have known what was coming.
Confirmation that Arsenal and Manchester City's failure to win their groups would condemn them to take the most difficult of paths to the quarter-finals of the Champions League came when they were paired with Bayern Munich and Barcelona respectively yesterday.
After Arsenal's nightmare in Naples and City's miscalculation in Munich, there was an air of inevitability their punishment would be the harshest possible against the two outstanding sides in European football over the past three seasons.
Wenger, of course, has been here before and having watched his side capitulate at the same stage in the first leg last year, the Arsenal manager will be hoping for a performance more like the 2-0 victory at the Allianz Arena was the spark that helped propel them into a fourth-placed Premier League finish.
It could have easily been another showdown with Real Madrid instead, with just Carlo Ancelotti's side and reigning champions Bayern remaining as possible opponents. But when Madrid were paired with Schalke, Arsenal's odds to win the competition tumbled from 16/1 to as low as 40/1 with some bookmakers in recognition of the task that now awaits them against Pep Guardiola.
Pellegrini's City had been the first to learn their fate when Luis Figo drew his former club Barcelona. That means a return to Catalonia for Yaya Touré, Txiki Begiristain and Ferran Soriano, although City's midfield general, director of football and CEO will know the first leg at the Etihad will be crucial.
"It's very tough, but we are happy because we are here and we will fight for the trophy," said Begiristain, who spent seven years at the Nou Camp in the same role he now occupies at City before leaving in 2010.
"It's a wonderful draw and these are two big teams so it's going to be great, great matches. The last game we played in Munich, winning against the champions of Europe, has given us a lot of confidence. We have shown we can score in all matches."
Both Sergio Aguero and Lionel Messi should be back to lead their respective sides by then and Pellegrini will be anxious that his Argentine striker makes a full recovery from an ankle injury.
Pellegrini revealed yesterday Aguero will be missing for 'at least a month' and he has an enviable record against Barcelona, having scored six goals in 11 appearances against them during his Atletico Madrid days. Should he return in time, Pellegrini will be confident his side can cause their opponents real problems if they can maintain their current form.
Yet the importance of City and Arsenal's group stage botches were underlined by the relatively favourable draws for Manchester United and Chelsea. Both completed the job on the final day matchday and will now face Olympiakos and Galatasaray in ties that look there for the taking on paper.
Neither will be totally straightforward, however, with the Greek side having finished ahead of Benfica in their group and currently on the back of a 10-match winning domestic run, while Roberto Mancini's Turkish champions were good enough to knock out Juventus last week.
The return of Didier Drogba for the second leg at Stamford Bridge will give the tie an extra edge, while Jose Mourinho will also be well acquainted with the threat of Wesley Sneijder having managed him to Internazionale's Champions League triumph.
Of the English contingent, though, it was David Moyes had most to celebrate. Europe has so far provided a welcome distraction to his travails in the Premier League and United should be too strong for a club that has reached this stage of the tournament for the first time in four seasons.
Elsewhere, Borussia Dortmund's reward for edging out Arsenal for top spot will be a tie against Zenit St Petersburg, who qualified for the last 16 despite earning just six points in the group stage.
Paris Saint-Germain will be strong favourites to reach the quarter-finals again after being paired with Bayer Leverkusen.
Milan, while the competition's sole remaining Italian representative, face a tricky encounter with Diego Simeone's dark horses Atletico Madrid.