#6 Jermaine Pennant (FC Pune City)
Pennant joined Arsenal as a youngster from Notts County in 1999. Arsene Wenger had big hopes from the speedy right winger, but somehow his Arsenal career never got off properly. He was loaned off to Watford, Leeds United, and Birmingham City, during his tenure at Arsenal. He managed to play just 12 games for Arsenal in the Premier League, and scored three goals.He once held the record of becoming the youngest ever player to debut for Arsenal.
The English winger joined FC Pune City in the 2014 ISL season, in what was a last minute addition for the Stallions. He managed to make just seven appearances for Pune in the ISL, but failed to live up to the expectations. He left the club and went on to join Wigan Athletic.