Carlo Ancelotti is the joint most successful coach in the history of the Champions League with three wins in the competition.
This will be his fifth final with two different clubs, though he has managed eight different sides in the competition.
Outside of Milan and Real Madrid, his best performance was the semi-final with Juventus in 1999, though he only took over in time for the quarter-final.
Here we take a look at his five finals so far
Milan vs. Juventus, 2003 – 0-0: Rossoneri win on penalties
It was a very Italian affair for Ancelotti’s first experience. As well as Juve in the final, Milan had to overcome derby rivals Inter in the semi-finals.
Despite reaching finals for three successive seasons in the early 1990s, Milan had disappointed towards the end of the decade and turn of the century.
The 2002-03 campaign was the first time they had reached the knock-out stages since 1995 – and they went all the way.
The final at Manchester United’s Old Trafford was a fairly forgettable 0-0 draw and it was Andriy Shevchenko who stepped up to fire home the winning penalty and bring home European Cup No. 6.
Milan vs. Liverpool, 2005 – 3-3: Rossoneri lose on penalties
Two years later and Milan were establishing themselves as the top dogs in Europe. Though they were lucky to reach the final after being outplayed for large parts by PSV Eindhoven in semi-finals.
Paolo Maldini gave them the lead against Liverpool in Istanbul within a minute and two Hernan Crespo goals put them in full control by half-time.
However, Liverpool completely turned it around and were level on the hour mark as Milan fell apart. The Rossoneri composed themselves and Shevchenko missed two golden chances to score in extra-time when he was thwarted by Liverpool goalkeeper Jerzy Dudek.
And Ukraine forward – then reigning Ballon d’Or winner – was the villain again as it was his missed penalty which handed Liverpool the trophy.
Milan vs. Liverpool, 2007 – Rossoneri win 2-1
Ancelotti’s only Champions League final to be settled inside 90 minutes. On this occasion, it was a different story in the semi-finals as Milan produced arguably their best performance under Ancelotti to hammer United 3-0 at San Siro.
Milan took the lead just before half-time when an Andrea Pirlo free-kick hit Filippo Inzaghi and found its way past Liverpool goalkeeper Pepe Reina and into the back of the net.
The goal was controversial as it hit the former Juventus forward’s upper arm but it was allowed to stand.
It was a tense second half but Inzaghi eventually settled Milan nerves eight minutes from time as he rounded Reina to put his side 2-0 ahead – and rendering Dirk Kuyt’s late goal irrelevant.
Real Madrid vs. Atletico Madrid, 2014 – 4-1 Los Blancos win aet
After disappointing showings at Chelsea and Paris Saint-Germain in Europe, Ancelotti had led Madrid to their first Champions League final for 12 years.
And again, produced a performance for the ages in the semi-finals as Madrid won 4-0 away to Treble-winners from the previous season, Bayern Munich, who were now led by Pep Guardiola.
In Lisbon for the final itself, Diego Godin gave Atletico a 36th-minute lead which looked to be enough until Madrid defender Sergio Ramos produced one of the competition’s most dramatic moments with a header in the third minute of stoppage time to send the match to extra time,
With Atletico deflated, Los Blancos took full advantage with Gareth Bale, Marcelo, Cristiano Ronaldo capping off the scoring.