2004: Zenden signs for Middlesbrough
Boudewijn Zenden signed for Middlesbrough on a free transfer following a successful season on loan at The Riverside from Chelsea.
The Netherlands international was deployed in a central midfield position, where he played 36 matches scoring five goals, and was voted Boro's Player of the Year.
His performances brought him to the attention of newly-crowned European club champions Liverpool, who signed him in summer 2005.
2006: Carrick moves to Man Utd
After two impressive seasons at Tottenham Hotspur, Michael Carrick moved to Manchester United in the summer of 2006.
A composed, ball-playing midfielder, Carrick took the No 16 shirt formerly worn by Roy Keane and became a mainstay in the Man Utd side over 12 seasons.
He lifted the Premier League Trophy on five occasions, helped United win the 2007/08 UEFA Champions League and made 315 PL appearances for the club.
Having made the sixth-most PL appearances for the Red Devils, and 481 in total for West Ham United, Spurs and Man Utd, Carrick announced his retirement in 2018 to take up a coaching role at Old Trafford.