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Al Ahli coach David O’Leary and his captain Fabio Cannavaro attend a press conference last Wednesday at the Emirates headquarters in Dubai. Image Credit: EPA

Dubai: David O'Leary will be jettisoned back to his Uefa Champions League heydays spent managing Leeds United tonight, as his new side Al Ahli faces Serie A table-toppers AC Milan in the Emirates Challenge Cup exhibition match — to be held at Rashid Stadium from 8pm.

AC Milan, in the UAE for their annual winter-camp, brings a full-squad of stars such as Robinho and Ronaldinho to test O'Leary's side (fourth in the UAE Pro League) which is captained by Italian 2006 World Cup winner Fabio Cannavaro.

The Irishman last pitched his technical wits against AC Milan during the successful Champions League cup run of Leeds in 2000-01. Having seen off AC Milan 1-0 at Elland Road, with a 1-1 draw at the San Siro, Leeds then qualified from their group at the expense of Barcelona and Besiktas.

Their second round saw them get the better of Lazio and Anderlecht.

They qualified second to Real Madrid before defeating Deportivo in the quarters and succumbing to Valencia in the semi-final.

Rags-to-riches story

This run epitomised the riches-to-rags story of Leeds United, which bankrupted itself in player purchases to get silverware under chairman Peter Ridsdale.

Despite the millions borrowed against future gate revenue no titles were secured and the team plummeted down the leagues in financial ruin. No doubt, O'Leary will pause for thought about that now infamous campaign as he puts his new side through its paces tonight.

They'll be no repeat of that win at Elland Road however.

"This is not a match about ‘Can we beat AC Milan?'. Let's not get carried away. I'm just so proud that players who would never have had the opportunity to play against some unbelievable players now have that opportunity."

Avoiding injuries

"I've taken big clubs into games like this, but it's the other way round now for me. AC Milan will want to avoid injuries and get a feel for the game again after their break," O'Leary said.

"But I just want the players to go out and enjoy the moment. I've got lads who would never imagine themselves playing against such wonderful stars — I've played and managed against Milan. Fabio and myself have grown up in football, but for the youngsters this is a fabulous opportunity," he added.