
In the home dugout will be Wenger, battling to bring a steady stream of success back to north London after 18 years in charge of the club amid heavy criticism from his own supporters that he and Arsenal have stagnated.
On the other hand, Van Gaal brings his United side to the capital with the 20-time English champions showing signs of progress as the Dutchman builds the foundations for the club's recovery from the David Moyes disaster.
With one point separating the teams going into the game, Arsenal and United have faced similar issues in the first 11 league games of the season. Both can boast frightening attacking talent but their campaigns have been hampered by crippling injury problems, highlighting the lack of balance in the squads and exposing their lack of defensive depth.
But while Van Gaal has only been in the job for a matter of months, is in the process of transforming the team and has declared it will take three years to get United challenging for the title again, Wenger has no such excuse.
Indeed, the source of much of the frustration among Gunners fans has been the sheer predictability of the current situation, with defensive injuries bringing to the fore the folly of not signing central defensive cover during the summer.
It has cost Arsenal the upwards momentum and title challenge they thought was on the cards following the FA Cup triumph in May and Wenger is being challenged over his stubbornness and refusal to adapt.
How can Wenger fix the engine when he doesn't even realise it's not working properly?
Van Gaal, for his part, almost takes pride in his own arrogance but those who have worked with him always describe him as an innovator, a man with few blind spots when it comes to coaching.
The 63-year-old is aware of the problems at Old Trafford and is working to address them, which extends beyond asking executive vice-chairman Ed Woodward to help him sign a centre-back and central midfielder in the January transfer window.
On United's injury problems, for example, Van Gaal is known to have taken advice on mistakes he may have made and is looking to bring in expertise to ensure it does not become a recurrent issue in the same way it has for Arsenal.
While Wenger is a one-man band, running the training sessions and making decisions on players and team selection alone, Van Gaal is known to welcome input from his backroom team.
In fact, Van Gaal wants to be challenged. He wants the likes of Ryan Giggs to offer strong opinions, to question him and debate.
The reward for Giggs is that he gets to run some training sessions and takes team meetings; the reward for Van Gaal is that it helps him make the right decisions.
Perhaps that is why Van Gaal can boast the likes of Jose Mourinho, Pep Guardiola and Frank de Boer as his proteges while Wenger has schooled no managers of real note.
One of the chief frustrations at Arsenal has been over Wenger's reluctance to change his tactics or set-up to cater for the challenges thrown up by different opponents, while his sometimes baffling substitutions point to an ingrained tactical naivety.
In his short time at United, Van Gaal has tinkered considerably with his system and selection to find the right balance and adapt to the opposition. It is the same approach that brought unexpected success as the Netherlands finished third in the World Cup this summer.
He has tried a three-man defence, he has dropped Wayne Rooney into midfield, he has played Angel Di Maria all across the pitch to find the optimum solution, with hours of tactical work being done on the training ground.
Famed for his commitment to bringing through youngsters, the likes of Tyler Blackett, Paddy McNair and James Wilson have all been heavily involved already. Over at Arsenal, an exciting young full-back Hector Bellerin watched on as away fans screamed for his introduction in the 2-1 defeat to Swansea last time out.
Having won domestic titles in three different leagues and managed the Dutch national team twice, perhaps Van Gaal benefits from having so many more experiences to draw on than Wenger, who has spent 18 years at Arsenal.
Van Gaal makes mistakes too, of course, and may well be regretting his decision to allow Danny Welbeck to join Arsenal come Saturday night.
But in the grander scheme, it still feels like two managers are taking their teams in very different directions.
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