Angel Martinez/Real Madrid/Getty ImagesMourinho's 100th Champions League game wasn't his best, but the Special One still added to his exemplary achievements in Europe.

The first time Jose Mourinho came to our attention in a Champions League night in Manchester, he was rampaging down the Old Trafford pitch towards Costinha and the rest of his Porto side as they snatched a last-minute equaliser against Manchester United to progress in Europe's top competition. Fists pumping, long black coat waving in the air, jumping for joy. The relatively unknown Portuguese manager had just helped an unfancied Portuguese side see off the English giants and the rest is history: Porto became European champions and Mourinho became the "Special One."

That was in March 2004. Fast-forward to November 2012 and Mourinho has chalked up his 100th match in the Champions League having been crowned European champion not once, but twice -- the second time with Inter Milan. You may have expected something special from the "Special One" for his century of matches in the competition, but instead he had to make do with a point against Manchester City at the Etihad Stadium and a second-place finish in Group D -- known as "Death" -- thanks to being pitted against the champions of England in Manchester City, Germany in Dortmund (the runaway leaders of the group) and Holland in Ajax.

Madrid should have won in Mourinho's 100th match in the competition. A pile of chances inside the first 15 minutes yet only one goal to show from it, pretty much a tap-in by Karim Benzema when he lost his marker Maicon. Los Blancos were worth much more than that. Sami Khedira, that deep-lying, ball-winning midfielder, had three good chances to get on the scoresheet, but his finishing was just that of a defensive midfielder. Cristiano Ronaldo, being fed a chorus of boos throughout on his return to Manchester -- the blue side -- had one lobbed effort cleared off the line and the rebound deflected wide. City looked to be in for a long night but the visitors could not capitalise on their chances.

Roberto Mancini's men soon changed their tactics and got more into the game, having more of the ball in midfield and creating more opportunities in attack. Yaya Toure was overworked in midfield but had plenty of help in the second half; as such City showed some of the desperate attacking football required when you're on the brink of an exit from the competition. Yet none of it fazed Mourinho's men much and, if anything, City looked more prone to their visitors' counter-attacking style.

Still, Madrid couldn't find a second that could have killed the game. Instead a penalty and a red card for what was a trip by Alvaro Arbeloa on Kun Aguero -- even though it did look soft -- enabled City to rescue a point. It wasn't enough to thwart their exit, but it also ended Madrid's hopes of finishing top of the group.

Not to worry. Maybe it was all part of Mourinho's master plan? After all, Mourinho's two Champions League triumphs have both come when his teams finished second in the group stage. Porto finished behind Madrid and Inter Milan were second behind Barcelona when he took the Italians to glory, ironically at the Bernabeu. Time for a third European Cup? Time for a second-place group finish. Give the opposition a false sense of security and all that.

His 100th game in charge may not have been one his best in the competition -- really, it was far from a classic. Yet it still serves to back up his "Special One" claims, however, as if the two Champions League medals he already has were not enough.

Mourinho is the youngest manager to make 100 matches in Europe's top competition, only the fifth ever to achieve the feat. He's not in bad company, either -- Alex Ferguson, Arsene Wenger, Carlo Ancelotti and Ottmar Hitzfeld are the other four. His record? 100 matches, 54 wins, 26 draws and 20 losses. A win ratio of 54 per cent. Not bad going, is it? It's not as high as his domestic record at the clubs he's managed, but playing in Europe offers a much stiffer challenge and one that Mourinho has passed with flying colours.

Now he'll look towards a possible 108th match in the competition and a hat trick of triumphs. Los Blancos are through to the last 16 thanks to Wednesday night's City draw, and Madrid eyes will be firmly on La Decima, the club's long-awaited hunt for a tenth European crown. A trip to Wembley at the end of May will also be pencilled in Florentino Perez's diary no doubt, the next box to be ticked after last season's wrestling of the La Liga crown from Barcelona. The Madrid president was in Manchester to present Mourinho with an award for his 100th game in the competition; I'm betting that a word in his manager's ear about how special it would be to mark the occasion by winning the competition probably wouldn't have gone amiss.

"There are great coaches who have never won the Champions League. I'm young and lucky enough to have won it twice," Mourinho said in a pre-match press conference ahead of the City clash. "But I've still got many years ahead of me to add to those two trophies."

Mourinho's first match in the Champions League was for Porto against Real Madrid. One of his biggest moments came in Manchester when he guided his Portuguese side to victory on aggregate and ultimately his first European success. His 100th game also came in Manchester.

Can Mourinho return to England with Madrid to claim his third, and Madrid's tenth, European crown in May? Don't bet against it.

Follow Nicholas on Twitter @nicholasrigg

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