It is not the first time Harry Redknapp has entered a cup draw and pulled the team generally considered the one to avoid. In 2007-08, when Redknapp had taken Portsmouth to the quarter-finals of the FA Cup, he assessed his options and concluded that, if he could just dodge Manchester United (away), his team might have the chance to go all the way.

Redknapp was on the golf course with his son Jamie when news of the draw against Manchester United (away) filtered through and onlookers were treated to the sight of a 60-year-old man lobbing his clubs about and cursing his luck.

Tottenham Hotspur were supposed to benefit from finishing top of their Champions League group, ahead of the holders Internazionale. They were supposed to reap the rewards of their derring-do; Redknapp's team were joint leading scorers at the group stage, together with Arsenal. Instead, at the draw for the last 16 in Switzerland, they were paired with Milan, the runaway Serie A leaders and seven-time European champions.

Redknapp's reaction, though, was not to run screaming through Spurs Lodge. It was not only Portsmouth's famous 1-0 victory at Old Trafford en route to lifting the FA Cup that reinforced to him that anything is possible in knock-out football. He truly believes that Milan, for all the prestige, the glamour names and the stylish red-and-black shirts, are beatable.

It is not difficult to imagine Redknapp browsing the Milan squad list and blowing out his cheeks in admiration. There is little he likes better than the seasoned professional who has bought the T-shirt and starred in the video, and Milan have a back catalogue of them. Alessandro Nesta, Gianluca Zambrotta, Clarence Seedorf, Gennaro Gattuso, Andrea Pirlo, Massimo Ambrosini … Redknapp's respect for them is total.

Yet all of them are the wrong side of 30 and, although the coach, Massimiliano Allegri, wishes to reinvigorate the team, placing a greater emphasis on youth, the process needs time and resources and he has continued to rely on the old guard. Of the six veterans only Seedorf is not currently considered a part of Allegri's strongest line-up. The identity of the man who has just supplanted him in attacking midfield is sure to raise an eyebrow. It is Kevin-Prince Boateng, who proved such an expensive failure during his 18 months at Tottenham.

Redknapp feels that his vibrant young team can get at Milan, in much the same way that United did at the same stage of last season's competition. Sir Alex Ferguson's side won 7-2 on aggregate, over-running Milan in midfield and exploiting the unwillingness of their forward players to track back.

Tottenham have exploded on to the Champions League scene and opponents, chief among them Inter, have been unable to cope with the pace of their attacks. It has been on the flanks where Redknapp's team have made capital and memories remain fresh in Milan of the way that Gareth Bale destroyed the Inter right-back Maicon in both of the group ties.

The Milan right-back is Ignazio Abate, the 24-year-old Italian, who stood up well to Cristiano Ronaldo's tricks and provocation when his team faced Real Madrid at San Siro in the group stage. Abate is noted for having pace. On the other flank Allegri will hope that Zambrotta's know-how will suppress Aaron Lennon.

Milan were among the clubs who wanted to sign Bale over the summer but he was not for sale. Their two marquee additions, though, have shone. Zlatan Ibrahimovic is the club's top scorer with nine in Serie A and four more in the Champions League while Robinho, perhaps surprisingly for English fans, has knuckled down to work for Allegri, who had informed him that Milan represented his last shot at the big time in Europe.

Robinho has established himself as Ibrahimovic's partner, ahead of the injury-prone Pato, who is currently in the United States seeing a specialist, and Ronaldinho, whose best days are in the rear-view mirror. Filippo Inzaghi is a long-term injury casualty. Tottenham, so open defensively, could face another shoot-out.

Allegri was appointed in the summer to replace Leonardo after he had impressed in the previous two Serie A campaigns at Cagliari, his only exposure to top-flight management. The 43-year-old, who is rated by Fabio Capello as the best young coach in Italy, was relieved to have avoided Barcelona and Chelsea in the draw. Redknapp intends to show him that he has not been so fortunate.