While he has had his share of dealings with both of those men during his time in England, for many his simmering battle against another relative newcomer - Liverpool's Spanish boss Rafael Benitez - has provided the most entertaining story.

Here, with another chapter about to be written, we look back at three memorable cup meetings between the two.

2005 League Cup final

Mourinho went into the match having established a reasonable level of dominance over his Spanish counterpart, winning both Premiership fixtures in his first season at Stamford Bridge.

But Benitez's reign at Liverpool has been characterised by their resistance in cup competitions and within a minute John Arne Riise put the Reds ahead.

For nearly 80 minutes that looked to be enough but then the inspirational Steven Gerrard turned the ball past Jerzy Dudek to force extra-time.

Antonio Nunez restored the lead following the restart only for sucker-punch goals from Didier Drogba and the struggling Mateja Kezman to seal a dramatic win for the Portuguese coach.

2005 Champions League semi-final

Fate brought the pair together again in European competition and by now there was palpable animosity.

Mourinho had enraged Liverpool fans with his finger-to-the-lips gesture in their previous cup meeting, but this time it was they who had the last laugh.

A goalless draw at Stamford Bridge cranked up the tension and, if anything, gave Liverpool reason for optimism in the return fixture.

Then, spurred on by an Anfield crowd who had no intention of 'shushing' for anybody, Liverpool grabbed another early goal.

This time it took four minutes for Luis Garcia to turn the ball in for a goal Jose Mourinho still regards as a "phantom" strike.

2006 FA Cup semi-final

Liverpool's league form against Chelsea continued to leave plenty to be desired, but following their controversial win on the way to a famous Champions League win in Istanbul, Benitez continued to be a thorn in Mourinho's side in knockout competition.

The sides were drawn against each other in the group stages of Europe in 2005/06 and on each occasion neither side could break the deadlock.

That meant that when the sides were scheduled to meet once more - this time in the last four of the FA Cup - both had a point to prove.

Again, it was Riise who got the ball rolling, converting a free-kick routine after 21 minutes before a Drogba equaliser and a superb Garcia strike - this time with no doubts about the validity - won it for Liverpool.