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.In the 2000–01 season, Bridge was an ever-present at left-back as Saints finished their final season at The Dell in tenth place in the Premier League table.As Southampton struggled to pick up points (with only two points after the first nine games), Bridge played (on the left wing) in most of Saints' league games until early December before losing his place to Hassan Kachloul.
This ended his season and also meant he missed the following weekend's League Cup Final.
His strong early season form, however, was not enough to hold down the left-back position, with Mourinho preferring Ashley Cole in most games.
Following Cole's injury in the 3–0 Premier League win against Blackburn Rovers early in 2007, Bridge became Chelsea's natural choice for left-back.
Bridge made 36 appearances for the England national team between 20, being selected for two FIFA World Cup squads and UEFA Euro 2004.
Bridge made his first senior start in the next match on 22 August in a 5–0 defeat away to Charlton Athletic.