solid performances at the 2006 FIFA World Cup earned him a trial and subsequent three-year deal with Dutch top flight club FC Twente despite reported interest from other Dutch clubs, including Ajax and PSV Eindhoven. His league debut for FC Twente ended badly when he was sent off in the first half, in a 3–0 loss against Heracles Almelo. After serving a two match suspension, Wilkshire made his return to the first team from injury, where he assisted one of the goals, in a 2–2 draw against AZ on 17 September 2006. It wasn't until on 12 November 2006 when Wilkshire scored his first Twente goal, in a 7–1 win over Groningen. The following month, on 27 December 2006, he scored his second goal of the season, in a 3–0 win over AZ Alkmaar. After suffering from a knee injury against ADO Den Haag on 28 January 2007, which saw him out for weeks, he made his return to the first team, coming on as a substitute in the second half, in a 0–0 draw against Willem II on 24 February 2007. He continued to feature in the first team for the remainder of the season and finished his first season, making thirty appearances and scoring two times in all competitions. Nevertheless, Wilkshire would go on to play regularly in the 2006–07 campaign which saw FC Twente qualify for the UEFA Cup. In the 2007–08 season, Wilkshire started well in the opening game of the season against Excelsior when he set up one of the goals, in a 2–0 win. Despite coming off in the five minutes to the game against Willem II on 16 September 2007, He then scored his first goal of the season, as well as, setting up one of the goals, in a 3–0 win over NEC on 23 September 2007. After setting three goals in two matches, including assisting twice against Feyenoord on 27 October 2007, Wilkshire scored his second goal of the season, in a 1–1 draw against NAC Breda on 10 November 2007. His third goal of the season later came on 23 March 2008, in a 2–1 win over Ajax. Despite being left out of the squad, either due to suspension and once left out of squad after he was late, due to an international commitment, he finished his second season at the club, making thirty-six appearances and scoring three times in