It became clear at the start of the 2008–09 season that King's injury problems meant that he could not play in every game. Ramos picked him in all five of the cup games he managed the club for that season, but only two of the eight league games. With Spurs rooted to the bottom of the league, having picked up just 2 points from those 8 games, Ramos was sacked and replaced by Harry Redknapp, who chose to prioritise the league and only play King in those games. On 26 October 2008, King made his 200th league appearance for Tottenham Hotspur as they defeated Bolton Wanderers 2–0. He captained the club in the League Cup final yet again, this time against Manchester United, keeping a clean sheet after 120 minutes of play, but Tottenham lost on penalties.