League difficult and he managed only one goal in a 4–1 defeat to Manchester United at Old Trafford on 8 December 2007. He also missed a vital penalty in a 2–1 home defeat to Blackburn Rovers on 30 December 2007. It proved to be his last contribution for Derby County, and the club confirmed there was interest shown in Howard from other clubs in December. Leicester City Howard joined Leicester City on 1 January 2008 for a fee of £1.5 million, signing a three-and-a-half-year contract. Initially signing on loan, Derby teammate Matt Oakley joined him at the club on 11 January. He made his debut in a 3–1 defeat to QPR on 1 January 2008. He scored his first goal in an M69 derby on 12 January, in which Leicester won 2–0. Howard bagged a hat-trick in a 4–1 win over West Brom on 15 March, a result he said was coming and was confident the club could stay up. Despite regaining his form by scoring six goals however, Howard could not prevent Leicester from being relegated at the end of the season. Desperate to win promotion back to the Championship, Howard was able to maintain his form the following season. Partnering teammate Matty Fryatt in attack, he scored 13 league goals and contributed numerous assists to help Leicester maintain their lead at the top of League One. He went on to help the club secure their promotion as champions, earning his second League One medal on 24 April. Howard was also voted Leicester City supporters club player of the season for the 2008–09 season. His overall performance earned him the club's player of the season award on 28 April 2009. In April 2009, Howard believed Leicester could win promotion to the Premier League in the 2009–10 season. He failed to score his first goal until 12 December 2009, in a 3–0 win over Sheffield Wednesday. Howard scored a total of 5 league goals in 35 matches as Leicester qualified for the Championship play-offs. Despite eventually going on to lose to Cardiff City 4–3 on penalties in the play-off semi-final, Howard's performance in the second leg earned him great plaudits, being described in both The Times and The Scotsman as "unplayable". Howard extended his contract with the club until June 2012 on 21 October 2010. He scored 4 league goals and played 35 games in the 2010–11 season, of which