Arsenal have finally reached their nadir in recent years after having been been kicked out of the FA Cup by Nottingham Forest.
The defeat seemed to top an iceberg of serious questions about the club's path that have began to weigh down in recent years - most vocally expressed by the supporters.
Wenger opted to give most of his first-starters a rest, and perhaps unsurprisingly the Gunners lost. But it was the nature in which they lost that raised questions.
Here are they key points observed from the game.
Did Arsenal sink into complacency?
The Gunners put up a spirited fight against Chelsea to come back from goal deficit at the Emirates last week. None of that was on sight against Forest.
The Gunners might have put in a shift with Welbeck's lifeline goal, but, overall, a level of desire and hunger was on show this match.
Complacency might have played a role here.
It all started with Wenger, who made a casual decision to rest key players for the contest. Not only that, but the French boss' decided to not even include them as a back-up option on the bench.
This, of course, backfired in a spectacular way.
What does the Arsenal bench bring?
The game raised a question over the quality of the depth of the squad.
Arsenal has a lot of personnel on the bench, and this seems good as regards to fitness and fatigue issues in the long-run, but the substitutes' dismal performance against Nottingham Forest showed none of the needed quality and mentality.
Theo Walcott, Per Mertesacker and Danny Welbeck were the man counted on. They did not deliver in any way.
Considering the transfer window is open, Wenger might do well to rethink the use of his fringe players. Performances such as this might make him more willing to cash in on any of them.
Is that it for Arsenal this season?
With the Gunner out of the FA Cup, many will ask what is left for them this season.
The League crown is far beyond reach as City are in pole position with a gigantic point-lead and now the FA cup, in which Wenger has enjoyed the most success, has evaporated.
It seems the only chance for trophy is presented by the Carabao Cup - and this might end too today as Arsenal play Chelsea over two legs in the semi-final. The Europa League seems like a possibility, but Wenger has not given an indication that he values it at all. So the Arsenal supporters seem to be in for a tough ride in the coming months.