Jose Mourinho will become the youngest coach to clock up 100 Champions League matches on Wednesday night at the Etihad Stadium. The 49-year-old beats previous record-holder Carlo Ancelotti who was 51 and joins other centurions Arsène Wenger, Ottmar Hitzfeld and Sir Alex Ferguson.
The Real Madrid coach might afford himself a wry smile that the fixtures have fallen in such a way that he reaches the milestone in England when he steps out before his side face Manchester City on Wednesday. There will be far greater recognition for his achievement there than back in Spain, where last week both he and Cristiano Ronaldo were ignored in the Spanish League's awards.
Ronaldo came third in the best striker category of last season and Mourinho was beaten by Pep Guardiola for the best coach award, despite Real Madrid and not Barcelona finishing on top of the league with the biggest points tally in the history of the competition.
If the lack of respect from awards voted for by Spain's professionals ahead of the final weekend of last season are difficult to understand, the ongoing frosty relationship between the two men and their own club is stranger still.
If you are a Real Madrid supporter what's not to like about the manager who has registered 100 wins faster than any other coach in the league's history, and the player who has reached 100 goals faster than any of the club's illustrious strikers?
Yet there were jeers from a minority of home supporters for Mourinho during the win over Athletic Bilbao at the Bernabeu on Saturday and the club has still set no date for new contract talks with Ronaldo. Both men talk of staying in Spain but have also admitted to missing the Premier League –Spain remains the love affair that just never got started.
Real were winning 5-1 on Saturday when the most vocal section of the Santiago Bernabeu began singing the coach's name prompting another section of the ground to drown out the homage.
It's a regularly-expressed difference of opinion among supporters. "It didn't happen at Chelsea, at Porto or at Inter," said Mourinho when the whistles were first heard.
"If they whistled [Zinedine] Zidane, if they whistled the other Ronaldo, if they whistled Cristiano Ronaldo, why are they not going to whistle me?"
Ronaldo remains more at odds with the club's directors than with its supporters. Fans applauded him during Saturday's game, despite him not scoring, but they support the club and not the player over the delay in offering him a new contract.
He currently takes home around €10m (£8.1m) annually. The now defunct Beckham law that previously meant big foreign signings only had to pay 24.75 per cent tax means any new Ronaldo contract would be subject to 52 per cent tax.
And with the club shouldering the fiscal burden, that means even if Ronaldo's take-home pay was frozen at €10m it would cost Real Madrid €20m a season.
They could pay more of his wages as image rights and then reduce the amount of those rights they rake back – currently around 50 per cent – but remain reluctant to do that leaving his future at the club beyond this season far from settled.
Ronaldo has said he would not join this week's opponents Manchester City as long as Sir Alex Ferguson remains at Old Trafford. Paris Saint-Germain looks like the only other club financially capable of moving him closer to the top of the table in terms of earnings.
Mourinho's contract also runs until 2016. Seeing it through at a club that has hired and fired 25 coaches in as many years would be almost as impressive as winning the league in four different countries.
This week's Champions League opponents were the favourites to take him last season but they kept faith with Roberto Mancini and have since hired Txiki Begiristain – a man with a track record of overlooking Mourinho.
The latest stick the Portuguese is being beaten with at Madrid is that he has done nothing to bring the club's youth players into the first team in the two and a half years he has been at the Bernabeu.
Based on albeit slightly generous estimated transfer fees, Catalan paper Sport last week claimed Barcelona's youth system had produced around £400m worth of talent over the last five years.
"I didn't sell Juan Mata, Alvaro Negredo and Roberto Soldado," said Mourinho who knows the boat carrying Madrid's golden generation of talent sailed long before he arrived. What is true is that success at Porto, Chelsea and Internazionale was achieved almost entirely without young players who Mourinho gave a debut too.
On Wednesday night, of Real's probable team only goalkeeper Iker Casillas and full-back Alvaro Arbeloa (who had to move to Liverpool to gain recognition) will have come through the youth system.
Should they win against City on Wednesday, Real will almost certainly be through to the last 16. Winning the club's 10th European Cup, and Mourinho's third, remains the priority.
"One day it will be my turn to respond and they will be left sad," he said of those first whistles at the singing of his name. Whatever he and Ronaldo go on to achieve at Madrid you get the feeling when the time does come to say goodbye the emotional ties will be cut painlessly.
"He's glad he didn't win the award" said Mourinho's assistant Aitor Karanka at the weekend when asked about the manager's reaction to not being voted best manager despite his historic league title.
As he goes for win number 55 in his 100th European match, and as Ronaldo runs down the wing in a Manchester football stadium for the first time since 2009, both men will have that strange sensation of being in enemy territory... and yet having left much of the real animosity behind them at home.
Room for sentiment: Ferguson and Ronaldo
Cristiano Ronaldo left Manchester United three years ago but the affection between the Portuguese and his former manager, Sir Alex Ferguson, is still strong. Here is their latest love-in :
Ronaldo on Fergie: He's a fantastic person. He taught me many things. He's like a father in football. I really miss him.
Fergie on Ronaldo: I'd like to think it would be [possible to come back to United]. What would you think his value would be? He's definitely unbuyable.