Manuel Pellegrini's side was paired with Barcelona and Arsene Wenger's men face Bayern Munich, but both clubs will feel the tough matchups were avoidable.
Manuel Pellegrini will not be convinced that Barcelona respresents the toughest draw his team could have been handed, but the Manchester City boss will still have a huge job on his hands to ensure that his side is back in Nyon for the quarterfinal draw in March.
The Catalan giants are not the frightening proposition they were three seasons ago, with their suspect defense being highlighted widely as the way in for opponents looking for an opening, but they remain a tough prospect for a City side playing in the knockout stage of the Champions League for the first time.
|ROUND OF 16 DRAW
Having come within one goal of toppling Bayern Munich to top Group D, the Citizens may be left kicking themselves for their inability to ensure an easier path. The visit of Lionel Messi, Neymar and Co. will represent the Etihad Stadium's greatest occasion to date, but will also be the biggest test of what this City side is capable of.
Arsenal, meanwhile, got the toughest draw of the lot, with Bayern set to visit the Emirates Stadium just as it did in 2012-13.
Arsene Wenger will tell his side that last season's second-leg win in Munich proves that it has a chance against the European champions. He'll also point to FC Hollywood's loss to Manchester City last week as further evidence that Pep Guardiola's men can be overturned. But in reality, he would have rather seen any other name come out alongside that of the Gunners.
Like City, the Premier League leaders could have won their group. In fact, they should have won it. Group F may well have been this season's "Group of Death," but having got themselves into a great position ahead of match-day six, they have ultimately paid the price for not finishing the job off in Naples.
Pep's Bayern look more likely than any side ever has to become the Champions League's first back-to-back winner. Two meaningless defeats to City and Arsenal, plus a Superpokal loss to Borussia Dortmund, represent their only defeats of 2013. And given the way they are playing under the former Barca boss, there might not be too many more losses in the cards in 2014.
Arsenal's 6-3 loss at the Etihad on Saturday gave clarity to the argument that Wenger's side can be overcome by a fast, penetrative opponent that puts the emphasis on the Gunners' defensive third, and Bayern will look to do exactly the same come February.
If only they had taken the chance had and topped their group, they might be relishing what lies ahead, instead of looking fearful.