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Isleworth-born Pidgeley came through the youth ranks at Chelsea before turning professional with the Stamford Bridge club in the summer of 2002. After being on the bench for Chelsea nine times part-way through the 2002-03 season Lenny eventually went on loan to Watford in September 2003, a deal which was initially intended to last for two months, but was eventually extended to the end of the season.
Pidgeley making 28 starts and one substitute appearances for the Hornets before his return to Chelsea for the pre-season of 2004-05, where he spent a total of ten games sitting on the bench, while once coming on as a substitute, while also getting splinters in his backside for England in October 2004 in a European under-21 Championship qualifier away to Azerbaijan.
The next season Lenny dropped out of favour a little bit at Stamford Bridge and sat on the bench just four times while starting his only game for Chelsea before he was released, that being a 1-0 away defeat at Newcastle on the final day of the 2005-06 season. A campaign which did see Pidgeley play one game for Millwall on an emergency seven-day loan at the end of November 2005 due to a 'keeper crisis at the New Den.
Pidgeley then moving to the Lions on a permanent basis in the summer of 2006 where he was in and out of the side during his three years at the Den, the 25-year old though going on to make 66 starts for Millwall, while spending 42 games as an unused substitute.
The goalkeeper did have a spell just outside London however when he went on loan to now relegated Blue Square Premier club Woking in August 2008. The deal was initially supposed to last for just one month but was then extended to the maximum 93 days due to Pidgeley's excellent form at Kingfield, the 25-year old making 17 starts in his three-month spell with the Cards.
It was back onto the bench for the rest of his Millwall career though when he returned to the New Den and it was therefore no surprise to see him released by the play-off finalists at the end of the season. Carlisle manager Greg Abbott sees him as a good replacement for Ben Williams though as he commented to BBC Radio Cumbria :
" Dennis (Booth) threw him at me last season but we couldn't do it then, and there was no need to do it then really because we had Tim Krul who came in and did an adequate job while Ben was gaining his form. Now he is in, he is a bright character, he has fitted in great, his attitude is spot on and we are hopeful that he can replace Ben and take that position forward for us.
" For one or two different reasons his career has gone slightly off track, and that does happen with goalkeepers. To be fair he is still a baby as a goalkeeper in terms of age, I think that keepers start reaching their peak around or about maybe 27 or 28, sometimes even later than that. They are a breed on their own aren't they goalkeepers but he has come in and his attitude has been first class.
" All that he wants to do now, is to prove, well probably prove to himself first and foremost, that he is a top goalkeeper and that he can kick on and get his career going forward again. The early signs are very, very good though and we have been really sat back looking at him thinking that he could be some player for us, and let's hope that he performs that way for us.
" What we are doing at the minute is that we are trying to make sure that everything is right for Carlisle, and that we are getting the best of everything I think on a one-year deal. Because if Lenny comes in and does well then he has got to be hungry because he has got a one-year deal. "
First Team Transfers 2009-10 : Click here