After nine years at Liverpool, during which time he won the FA Cup and League Cup, McManaman moved to Real Madrid in 1999. The transfer became one of the most high-profile Bosman rulings of all time. He became the first English player to win the UEFA Champions League with a non-English club in 2000, and two years later became the first English player to win the Champions League twice. He also won La Liga twice before moving to Manchester City in 2003. He retired from playing in 2005. Since his retirement, he has worked as a football pundit for Setanta Sports, ESPN and BT Sport.