The following season carried on in a similar vein with Bridge making occasional appearances on the left wing until injuries to Francis Benali and the poor form of his intended replacement Patrick Colleter gave Bridge the opportunity to play at left-back, where he soon became a fixture in the Saints starting line-up.In the 1999–2000 season, he made 15 starts (plus four substitute appearances) scoring his first senior goal, with a powerful free-kick over the wall, in the final match of the season on against Wimbledon, as a result of which Wimbledon were relegated to Division 1 after 14 years in the top flight.

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He made his debut in a 2–1 defeat to West Ham United at Upton Park.

The move seemed to benefit him as he managed to secure his place in the 2006 World Cup English squad for the tournament in Germany.

Frankie Sandford and Wayne Bridge were married in front of famous friends and family yesterday.

The Saturdays star and footballer Bridge tied the knot at Woburn Abbey in Bedfordshire - where they were joined by Frankie's bandmates Una Foden, Vanessa White, Mollie King and Rochelle Humes.

Bridge's temperament and consistency, together with a high level of fitness, enabled him to continue to play every match until 18 January 2003 when he limped off with an injury in a 1–0 defeat to Liverpool. His finest moment came in the Champions League quarter-final against Arsenal in 2003–04.

Bridge scored the winning goal in the 88th minute to send Chelsea into the semi-finals and end an 18-game winless run against Arsenal. Bridge started the 2004–05 season playing regularly under new manager José Mourinho, but he picked up a serious ankle injury in an FA Cup tie against Newcastle United on 20 February 2005.

Bridge played the full match in Chelsea's 3–0 victory over Manchester City on the opening day of the 2006–07 Premier League season, providing a telling cross for the third goal, scored by a header from Didier Drogba.

His strong early season form, however, was not enough to hold down the left-back position, with Mourinho preferring Ashley Cole in most games.

and Bridge faced a challenge to get back into the side when he recovered from the injury that kept him out of the team in the latter stages of the 2004–05 campaign.