The Gunners have been drawn against holders Barcelona in the last 16 of the Champions League and Wenger will be contemplating the likelihood of an exit in the first knockout round for a sixth season in a row.
It took an enormous effort for Arsenal to drag themselves back from the brink of elimination in the group stage of this season’s competition after three defeats in their first four matches.
They produced their performance of the year to beat Olympiacos 3-0 last week and scrape into Monday’s draw.
The reward? Two matches against Lionel Messi, Luis Suarez and Neymar.
No Arsenal supporter genuinely expected to become European champions this season and there is an acknowledgement that the squad is still way behind the likes of Barcelona, Bayern Munich and Real Madrid.
The hope was that the team could at least break through the plateau of their annual exit in the last 16.
That now looks almost impossible. Groundhog Day has struck Wenger in the Champions League again.
Arsenal could curse their luck, but last year they whooped for joy when they were drawn against Monaco. However, the team still blew it and were knocked out by the Ligue 1 club.
After Arsenal finished second in Group F behind Bayern Munich, they knew they faced the prospect of being drawn against one of the superpowers of European football.
And so it transpired as they were handed the worst possible draw.
Arsenal were knocked out by Barcelona in 2010 and 2011 - and it seems inevitable that history will again repeat itself in 2016.
Wenger has shown over the last year that he is willing to change his approach to big matches and the Gunners will look to pack men behind the ball and counter-attack in a similar manner to the way they played in the 2-0 home win over Bayern in October..
The backline has improved with the arrival of goalkeeper Petr Cech and only Manchester United have conceded fewer goals in the Premier League.
But holding off Barcelona is a completely different prospect, particularly with main defensive midfielder Francis Coquelin out with knee ligament damage and unlikely to return in time for either leg in February and March.
The silver lining for Arsenal is that they are likely to have fewer distractions when it comes to their main goal for the season of winning the title for the first time since 2004.
Title rivals Manchester City will be expected to progress past Dynamo Kiev into the quarter-finals, while Manchester United will have to play nine matches in the Europa League should they make it all the way to the final.
It is probably the only posit
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