be going nowhere except Macclesfield reserves if he doesn't improve." The club insisted that Whitaker was too valuable a player to let go. This transfer talk came despite him having recently signed a contract to keep him with the "Silkmen" until June 2005. Rated as a star player before the start of the 2003–04 season, he had a rather quiet season with just six goals, going 22 games without a goal from November to the season's finish. He scored just four goals in the 2004–05 season, though manager Brian Horton was still keen to hold on to him, despite nine others being deemed unworthy of a new deal. Six goals in 45 appearances followed in 2005–06. However, despite having been established in the heart of the Macclesfield midfield for the past four years and winning the club's player of the year award, he was released at the end of the season. Port Vale Now a free agent, Whitaker moved up to League One with Port Vale in June 2006. He played 51 games in his first season at Vale Park. At the end of the 2007–08 season, where Whitaker again played 40+ games, he was offered a new contract along with three other Port Vale players. But in May he rejected the contract and was told he could look for another club. However, Lee Sinnott told Whitaker that he would get back to him with a better offer if chairman Bill Bratt could raise some more money, the wage bill having been cut due to relegation. In June, he was offered an improved deal. Whilst mulling over the offer he was given a deadline. On 20 June 2008, he turned down the chance to stay at Vale, and instead opted to join Oldham Athletic, still in League One. Oldham Athletic Whitaker scored eight goals in 42 appearances for the "Latics" during the 2008–09 season. He was released at the end of the 2009–10 season, despite missing only a handful of games during his spell at the club. Chesterfield Whitaker was signed by Chesterfield in May 2010, linking up with his old boss John Sheridan. He started the 2010–11 campaign with three goals in as many league games, having bagged a hat-trick against Hereford United. Playing in every one of the club's league games, scoring fifteen goals in the process, Chesterfield won promotion as champions of League Two. He was also