#2 William Gallas (17th Aug, 1977)/Andre Villas-Boas (17th Oct, 1977)
The versatile Frenchman just makes it to the list. He played a season under Andre Villas-Boas at Tottenham Hotspur in 2012-13. Both at 35, William Gallas was just two months elder than his manager Villas-Boas, when the two worked together.
The ex-Chelsea and Arsenal star concluded his Premier League stay at Tottenham Hotspurs. Having spent four defining seasons at Arsenal, the player demanded a contract that was simply not entertained. The move saw Gallas becoming the first man to play for all the three London based clubs. He was 33 by the time he arrived at White Hart Lane.
In 2012-13, after playing 2 years for the Lily Whites, Gallas saw Tottenham appoint Andre Villas-Boas as the head coach in a three-year deal to replace Harry Redknapp. The defender made 17 appearances for the club under the Portuguese before he was released at the end of the 2012-13 campaign.