An improved deal was signed in March 2009 which contracted him to Spurs until 2014. Lennon finished the 2008–09 season as the Tottenham Fans' Player of the Season, the club's Player of the Season and Young Player of the Season, and was nominated for a third successive year for PFA Young Player of the Year, this time losing out to Ashley Young. He played in 47 matches in all competitions and scored five goals, including a late equaliser in a memorable North London derby which ended 4–4 and was manager Harry Redknapp's first match in charge. Spurs finished eighth in the league and reached the 2009 League Cup Final, which they lost on penalties to Manchester United after a goalless draw at Wembley Stadium.