Ashton made an impressive start to his West Ham career, making his debut in the Hammers' 3–2 victory away to Arsenal, and scored some key goals in West Ham's following fixtures, including two goals in the FA Cup quarter-final against Manchester City, which was vital in continuing the team's inspiring FA Cup run in 2006. In West Ham's semi-final against Middlesbrough, Ashton broke Middlesbrough goalkeeper Mark Schwarzer's cheekbone. He caught Schwarzer with his elbow in an aerial challenge in the first half. This incident did not go well with the Middlesbrough fans, who booed Ashton for the remaining time he was on the field. Ashton however, made an apology to Schwarzer and to 'Boro fans and said that it was accidental and that no malice was intended.