The two clubs went head-to-head for the title in the early 2000s with legendary managers Sir Alex Ferguson and Arsene Wenger vying for top spot.
But those days are long gone with Manchester United still struggling in the post-Ferguson era and Arsenal finding their feet under Unai Emery.
Both clubs appear to be miles away from challenging Manchester City and Liverpool for Premier League success.
In fact, Arsenal and United even missed out on Champions League qualification, finishing fifth and sixth respectively last season.
And from aiming for Premier League titles, the priority now seems to be trying to return to the top four.
When the two sides meet on Monday, United will not have a Ruud van Nistelrooy or a Wayne Rooney leading the line.
Instead, they could be relying on 17-year-old Mason Greenwood or Anthony Martial, who is not fully fit.
Old Trafford boss Ole Gunnar Solskjaer feared Marcus Rashford could be sidelined ‘for a while’ with a groin injury after being forced off in last weekend’s 2-0 defeat to West Ham.
United’s no.9 options are light after failing to sign a replacement for Romelu Lukaku, who joined Inter Milan for £72million in the summer.
The Manchester United of old would never have gone into a season without a recognised striker.
Rashford and Martial have featured through the middle this term, but have spent the majority of their careers playing as wingers.
Arsenal, meanwhile, will not have a player like Patrick Vieira to control and dominate the midfield.
Instead, they are likely to be relying on Granit Xhaka, who has come under-fire for his early-season form, which included giving away a needless penalty in a 2-2 draw with Tottenham.
Manchester United addressed their leaky defence by making Harry Maguire the world’s most expensive defender after paying Leicester £80million last month.
While Maguire and Victor Lindelof have shown signs of becoming a good pairing, they are no Rio Ferdinand and Nemanja Vidic.
And Arsenal’s first-choice defensive partnership of David Luiz and Sokratis Papastathopoulos is a far cry from Martin Keown and Tony Adams.
Both managers seem to be under pressure, too.
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