Milan are the stand-out side from the seven group stage runners-up Villas-Boas' side could be paired with at UEFA headquarters in Nyon. Having narrowly won their group, Chelsea managed to steer clear of the likes of fellow table-toppers Barcelona, Real Madrid, Bayern Munich and Inter Milan.
But that would mean little if they are drawn against seven-time European champions AC Milan, and Villas-Boas said: "There are, of course, a lot of top teams also in those runners-up spots. One team with seven European titles and, for sure, those will be the ones to try to avoid."
Basle scream out as the dream draw following their against-all-odds victory that knocked out Manchester United last week.
But, beyond that, any one of Napoli, Marseille, Lyon, Zenit St Petersburg and CSKA Moscow will present challenges - the latter two particularly as a result of the freezing temperatures in Russia in February and March.
Arsenal also won their group and face the same potential opponents barring Marseille, who finished runners-up, and instead could meet Bayer Leverkusen, who were second in Chelsea's group.
It will certainly be easier without Manchester United and Manchester City, who will be in the Europa League draw immediately after the Champions League last-16 fixtures are revealed.
As one of the four best third-placed sides to have dropped out of the Champions League, they will face either one of the four worst third-placed sides or one of the runners-up from the Europa League group stage.
Ajax, Porto, Trabzonspor and Plzen are therefore possible opponents, as are Lazio, Red Bull Salzburg, Steaua Bucharest, Wisla Krakow and Lokomotiv Moscow.
The Manchester duo will be joined in the draw by Stoke, who finished runners-up in Group E, while Tottenham, Birmingham and Celtic will not be in the draw after being knocked out on Thursday night, along with Fulham who went out on Wednesday.
Source: PA
Source: PA