CHELSEA are planning an audacious attempt to sign Aaron Lennon from Tottenham Hotspur. The Barclays Premiership champions, who play at White Hart Lane tomorrow, will make a discreet inquiry about the England winger’s availability when the transfer window opens on January 1, but are more confident of securing his signature next summer.

Lennon has 3½ years left on his contract and it will take a fee in excess of £20 million to persuade Tottenham to sell, with Chelsea hoping to use Shaun Wright-Phillips as the makeweight in the transfer.

Wright-Phillips, 25, who cost Chelsea £21 million, has made little progress after failing to impress during his first season at Stamford Bridge and José Mourinho views Lennon, 19, as a much better prospect.

With Joe Cole and Arjen Robben already in his squad, Mourinho, the Chelsea manager, appears to be well blessed with wingers, but Chelsea’s ambition is to collect the best young players in the world and Frank Arnesen, Chelsea’s head of development and scouting, has convinced the club’s board that Lennon falls into that category.

Having recommended the former Leeds United winger to Tottenham before his controversial switch from White Hart Lane to Stamford Bridge 18 months ago, Arnesen is the driving force behind the move. Tottenham inserted a clause preventing Chelsea signing any of their players for a year when the £6 million compensation package for Arnesen was agreed, but that cooling-off period has passed.

Lennon would be eligible to play in the Champions League if Chelsea get their man in January. Uefa rules allow them to add three players to their squad for the knockout stages, one of whom can have played in the Uefa Cup.

Like Arnesen before him, Lennon would more than double his £25,000-a-week wages if he moved to Stamford Bridge, but whether he is prepared to sacrifice the virtual guarantee of first-team football remains to be seen.

The experience of Wright-Phillips provides a salutary lesson that the biggest clubs are not always the best places for young players to nurture their skills. He has started only 12 league matches since his move from Manchester City in July 2005.

In contrast, despite several injuries, Lennon has made 26 Premiership starts for Tottenham in 18 months at the club. His speed and trickery have enabled him to become a Spurs regular over the past 12 months and, after the banishment of David Beckham, he is well placed to challenge for a place in Steve McClaren’s first XI, with the England head coach committed to building a team based on pace.

Such progress has not gone unnoticed by Mourinho, who believes that Lennon uses the ball more intelligently and has greater potential than Wright-Phillips.

Losing Lennon to their bitter rivals would be a huge blow to Tottenham fans, but Martin Jol may take a more pragmatic view. The head coach is a huge admirer of Wright-Phillips and may find a cash-plus-player exchange hard to resist if the money was right.