Paul Konchesky joined London club Charlton Athletic as a trainee in the summer of 1997 and he went on to become the youngest player to represent the first-team before the record was later broken by compatriot JonjoShelvey. Paul Konchesky became the youngest first-team appearance maker at Charlton Athletic against Oxford United at the age of just 16 years and 93 days. However, he didn't become a regular at Charlton Athletic until he made 27 appearances for the first-team squad during the 2000/01 season.

Konchesky became frustrated at the lack of first-team opportunities at his left-back spot at Charlton Athletic and that prompted him to seek a move away from the club via a transfer request, but there were no serious takers. His transfer request was granted but there were no serious interests in him. The lack of interest in his services prompted him to join fellow London team Tottenham Hotspur on loan.

Paul Konchesky officially joined Spurs on loan from Charlton in September 2003 and he was at the club for some months. The initial agreement was a one-month loan deal before it was extended for one more month and then until January 2004. The English left-back was keen to secure a permanent transfer to Spurs, but Charlton officials wanted him to return to the club amidst their injury crisis. He was recalled by Charlton Athletic in December 2003 in addition to being taken off the transfer list. He would go on to spend one more season at Charlton Athletic before moving to another London club in West Ham United.
The Hammers paid around £1.5m to sign Paul Konchesky from Charlton Athletic on the back of his lengthy stay at the club. He scored six goals in 168 appearances for the Addicks and a further 15 appearances during his loan time with Spurs.