José Mourinho celebrated his 100th UEFA Champions League game as a coach last week as Real Madrid CF qualified for the round of 16 with a draw at Manchester City FC.

He joins an elite group of men who have overseen a century of games in football's premier club competition. Carlo Ancelotti was the last coach to reach three figures, following in the path of Sir Alex Ferguson and Arsène Wenger (who will get to 150 on matchday six). UEFA.com looks back on five of Mourinho's most memorable moments in the UEFA Champions League.

Manchester United FC 1-1 FC Porto: 2003/04 round of 16, second leg

Despite a comfortable passage through the group stage, Porto started as underdogs when drawn against United in the round of 16. Sir Alex Ferguson's side duly took the lead in the first leg at the Estádio do Dragão, but two goals from Benni McCarthy turned the tie on its head. Even so, United still looked likely to advance after leading for much of the return fixture at Old Trafford – until Costinha's last minute-strike earned Porto a 1-1 draw and sent them through 3-2 on aggregate. A jubilant Mourinho embarked on a famous dash down the touchline with arms raised in celebration. Europe had witnessed the birth of 'the Special One'.

FC Porto 3-0 AS Monaco FC: 2003/04 final

The Dragons followed up their 2003 UEFA Cup success by lifting European club football's most coveted trophy 12 months later. Playmaker Deco provided the creative spark for Mourinho's disciplined side in Gelsenkirchen as they surprised Europe by reclaiming the trophy for the first time since 1987. Free-scoring Monaco, who had overpowered RC Deportivo La Coruña 8-3 in the group stage, were expected to provide Porto with a sterner test, yet the Portuguese champions made light work of their opponents and sauntered to victory courtesy of goals from Carlos Alberto, Deco and Dmitri Alenichev. The final whistle sparked wild celebrations, although Mourinho's thoughts were already turning to the bright lights of the Premier League.

Chelsea FC 4-2 FC Barcelona: 2004/05 round of 16, second leg

Trailing 2-1 from the first leg, the Blues showed they had the style to compete on the biggest of stages under new boss Mourinho, combining thrilling thrust with a new spirit. Barça were blown away in the first 20 minutes as quick-fire strikes from Eidur Gudjohnsen, Frank Lampard and Damien Duff swung the tie in favour of the home side. Mourinho nonetheless needed to inspire his troops to dig deep as two goals from Barcelona hauled the visitors level. John Terry then secured a remarkable 5-4 aggregate victory by heading in a corner with 14 minutes remaining, proving that the man in the Chelsea dugout was far from a one-season wonder.

FC Barcelona 1-0 FC Internazionale Milano: 2009/10 semi-final, second leg

The Serie A side had never previously scored against Barcelona, but they broke that spell by engineering a 3-1 first-leg success at San Siro. Thiago Motta's dismissal 28 minutes into the Camp Nou return only served to strengthen Inter's resolve, and despite Gerard Piqué's neat turn and finish six minutes from time, the visitors' focus and rugged rearguard action took them through to the final. "My side are a team of heroes – the players left their blood on the pitch tonight," said Mourinho. "I have won the Champions League before, but tonight was even better because until the last minute I wasn't sure we would go through. This is bliss."

FC Internazionale Milano 2-0 Bayern München: 2009/10 final

The Portuguese tactician renewed his love affair with the UEFA Champions League as the Nerazzurri ended a 45-year wait for the European Cup to add to the Italian league and cup double they had already secured. Bayern started brightly enough before two unerring Diego Milito finishes in each half captured Inter's third continental crown and the second for Mourinho, who became just the third coach after Ottmar Hitzfeld and Ernst Happel to win the title with two clubs. Their triumph once again bore all the hallmarks of Mourinho's meticulous approach to management and paved the way for another chapter in his engrossing career.