From Martin Keown versus Ruud Van Nistelrooy to Patrick Vieira versus Roy Keane and, of course, Alex Ferguson versus Arsene Wenger, it remains one of the most hotly contested fixtures in the calendar.
And this midweek these two Premier League giants lock horns once again in what could prove a huge evening for both clubs, who arrive at Old Trafford off the back of very different weekends.
While Arsenal stormed past Spurs in an epic North London derby to go fourth, Man Utd slumped to a 2-2 draw with Southampton which leaves them down in seventh, a full eight points behind the Gunners.
But the good news for Mourinho’s men is that Arsenal have lost their last three midweek Premier League games (Tuesday, Wednesday, Thursday), conceding three goals in each defeat (vs Swansea, Man City and Leicester last season).
And they lost both Premier League meetings with Manchester United last season, while Manchester United are unbeaten in their last 11 home Premier League games against Arsenal (W8 D3), since a 0-1 loss in September 2006.
But Wednesday’s clash will provide some sore memories for the Red Devils, who host Arsenal in a midweek Premier League match since May 8th 2002, when Arsenal won 1-0 to clinch the title thanks to a Sylvain Wiltord strike.
And with Pierre-Emerick Aubameyang having scored with each of his last 10 shots on target in the Premier League, they will have to improve at the back.
United have conceded 23 goals in their 14 league games this season; it wasn’t until their 30th Premier League game of 2017-18 that they conceded their 23rd goal last season.
Mourinho, though, has never previously lost in five meetings with Arsenal manager Unai Emery (W4 D1, all in La Liga), with this their first meeting since October 2013 (Mourinho’s Real Madrid beating Emery’s Sevilla 4-1).
The stakes are high. The pressure is on.