The Portuguese has not always been the Frenchman’s biggest fan, having become embroiled in various touchline disputes down the years and infamously branded the long-serving Gunners boss “a specialist in failure”.
Mourinho can, however, relate to the situation Wenger currently finds himself in, as his position at Emirates Stadium continues to be called into question after 20 years at the helm.
His old adversary believes greater respect needs to be shown to an iconic figure of the modern era and has expressed a desire for Arsenal to ensure that Sunday’s meeting between the pair is not their last in the Premier League.
"I feel sympathy for all the other managers because we live through the same pain. Everyone," Mourinho told reporters.
"Football has changed. Now it is a game that makes it impossible for managers to stay in their position for a long time.
"Football now means if you don't get success then you are gone -- so yes, I feel bad for other managers. When you are at one club for 20 years it is impossible to have success every single year. Even Sir Alex will tell you that.
"The truth is that I hope Wenger keeps his job at Arsenal. I really do. I hope that the club trusts him to make things better. I think that Arsene is probably the last example of a manager who brings stability to a club over such a long time.
"Sir Alex was the same at United and he was able to leave when he knew it was time to leave. I hope that it is the same with Wenger. Why not?"
While Wenger has faced plenty of criticism this season, Mourinho has been offered the support required to continue a rebuilding job at United.
He has been unable to position them in title contention but has lifted the Community Shield and League Cup, with potential Europa League success to come.
Mourinho considers that to be a productive campaign and enough for him to be able to ignore any questions regarding his role from outside of Old Trafford.
He added: "I don't care what people think about me. I think this has been a good season and it can still be a very good season.
"In terms of my work, I think this has been about rebuilding a team and rebuilding a club. For me, it has been a positive process.
"What people on the outside say is what they will say - and it doesn't matter. It's not important to me because I know the work that we have done this season."