Jose Mourinho will go head to head with Madrid in the final of the International Champions Cup just three months after his acrimonious departure from the Spanish giants.
After feeling unloved for much of his time in Madrid, the Portuguese coach is enjoying his second spell at Chelsea, where he is treated with total respect following his Premier League title triumphs in 2005 and 2006.
The hero worship that follows his every move in the Premier League is a far cry from the hostile reaction to his presence in Spain.
By the time he departed Madrid, Mourinho had made numerous enemies among the squad, with his decision to drop iconic goalkeeper Iker Casillas an especially sore point, as well as falling out with some of the club's hierarchy, while fans jeered the manager in the final weeks of last season.
However, Mourinho's exit and the arrival of the more affable Carlo Ancelotti as his replacement has been the trigger for the kind of spending spree that the out-spoken 50-year-old would have relished.
While Mourinho was always given fairly substantial funds for signing during his time at Madrid, since his exit Real owner Florentino Perez has given the green light to a spending spree that is likely to approach £150 million ($230 million, 170 million euros) by the close of the transfer window.
In a bid to make a fresh start after Mourinho's divisive spell, Perez has already splashed out £63 million on Asier Illarramendi, Isco, Daniel Carvajal and Casemiro.
But the biggest purchase is still to come, with the nine-time European champions on the verge of signing Wales winger Gareth Bale from Tottenham for a world record fee of around £85 million.
If the Bale deal goes through it will be the fifth successive time Real have broken the transfer record.
Since signing Luis Figo for £37 million in 2000, Real have gone on to shatter their own record with swoops for Zinedine Zidane, Kaka and Cristiano Ronaldo.
Yet none of those deals occurred during Mourinho's reign and he may be wondering why he wasn't afford such riches.
Perez is also reported to have rubber-stamped a new five-year contract to keep Ronaldo onside after some trademark pouting from the forward last season, with the lucrative deal set to increase his annual salary to £14.8 million after tax.
Little wonder that Mourinho, speaking to ESPN on Sunday, took the opportunity for a swipe at Madrid's culture of political intrigue.
"Madrid is politics. Madrid is not about football, Madrid is not about sport," he said.
Mourinho also had a dig at Ronaldo by declaring "the real Ronaldo" was the Brazilian international who featured for AC Milan, Real Madrid and Barcelona, where the two worked together during Mourinho's tenure as translator and assistant coach in 1996 and 1997.
Madrid's spending is in stark contrast to the more austere times at Stamford Bridge.
While Mourinho was given a king's ransom during his first spell at Chelsea, billionaire owner Roman Abramovich keeps a tighter hold on his cheque book these days.
Mourinho had coveted the likes of Radamel Falcao and Edinson Cavani this summer, but missed out on both.
With Chelsea's interest in Wayne Rooney yet to persuade Manchester United to part with the England striker, Mourinho's biggest signing since returning is the £18 million move for Bayer Leverkusen forward Andre Schurrle.
In the circumstances, Mourinho would clearly relish the opportunity to give his former employers a reality check in Wednesday's glamour friendly.
But Mourinho's comments have fired up Real as well, with Ronaldo responding by saying: "We are facing Chelsea, not their coach. Although it's like any other game, we want to win.
"As we say in Portugal: 'I don't spit on the plate I eat on'. That's how I feel. I prefer to try and remember the positive side (to Mourinho)."