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 he reaches the milestone in England. There will be far greater recognition here than in Spain where last week both he and Cristiano Ronaldo were ignored in the Spanish League's awards for last season. Ronaldo came third in the best striker category, and Mourinho was beaten by Pep Guardiola as best coach, despite Real Madrid winning the league with a record points tally.
But if that is strange, the frosty relationship between the two and their club is stranger still. If you are a Real Madrid supporter what's not to like about the manager who has won 100 games faster than any coach in the league's history, and the player who has scored 100 goals faster than any of the club's strikers?
Yet there were jeers from a minority of home supporters for Mourinho in the win over Athletic Bilbao at the Bernabeu on Saturday and the club has still set no date for new contract talks with Ronaldo. Real were winning 5-1 when the most vocal section of home fans began singing the coach's name prompting another section to drown out the homage.
Ronaldo remains more at odds with the club than its fans, who support the club over the delay in offering him a new contract. He currently takes home around €10m (£8.1m) a year, but law changes mean that any new contract would be subject to 52 per cent tax. And with the club paying it, that means if Ronaldo's pay is frozen it would cost the club €20m a season.
Ronaldo has said he would not join Manchester City as long as Sir Alex Ferguson is at Old Trafford. Paris Saint-Germain looks like the only other club financially capable of affording his wages.
Mourinho's contract also runs until 2016. Seeing it through at a club that has fired 25 coaches in as many years would be almost as impressive as winning the league in four different countries.
Should they win against City they 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 the whistlers. Whatever he and Ronaldo achieve in Madrid you feel when they say goodbye the emotional ties will be cut painlessly.