As a result of their failure to win their group, Arsenal is been drawn with the winners of other groups and makes their progression to the next round an uphill task in recent years.
However, this time around, the Gunners, who finished second to Borussia Dortmund, have been dealt a more favourable tie in the form of Ligue 1 outfit, Monaco.
It’s somewhat of a romantic draw for Arsenal boss, Arsene Wenger, who managed Monaco between 1987 and 1994, totally transforming what had been an ailing club in the process.
In signing the likes of Glenn Hoddle and George Weah, Wenger was able to guide Monaco to their first Ligue 1 title and Coupe de France triumph in six years.
On Wednesday, the 65-year-old will come up against his former employers for the first time since he departed for Japan.
In terms of team selection, Wenger is likely to be without the injured midfield duo of Aaron Ramsey and Alex Oxlade-Chamberlain, which could well tempt the Frenchman to stick with the same side that started Saturday’s 2-1 win over Crystal Palace.
During his stint in the Premier League with Tottenham Hotspur, Manchester United and Fulham, the Bulgarian frontman found the net on three occasions against Arsenal.
The North Londoners do not have an overly positive home record against French clubs, having only won half of their 10 matches.
In contrast, Monaco, who are currently fourth in France’s top flight, have traditionally done well during their trips across The Channel, with just one defeat coming from five encounters.
Arsenal possible starting lineup: Ospina; Chambers, Mertesacker, Koscielny, Monreal; Coquelin, Cazorla; Ozil, Sanchez, Welbeck; Giroud.
Monaco possible starting lineup: Subasic; Fabinho, Wallace, Abdennour, Kurzawa; Toulalan, Kondogbia; Moutinho, Martial, Carrasco; Berbatov.