following an appearance at the Welsh International Super Cup, where he was named the Golden Boot Winner, scoring 14 goals in 5 matches.

After a brief trial with the VfB Stuttgart U19 side, he signed later on that summer and remained with them till the end of 2001.

[2] After leaving Stuttgart, he had agreed to join Hungarian side MTK Budapest, but three days later they had a match in Belgium, where he instead signed a five-year contract with Belgium first division side Royal Antwerp FC, although due to complications with getting his ITC from Canada, he was limited to playing in only exhibition matches for three months.

[4] He helped Hamilton win their first title as Western Conference champions, although they were eliminated in the semi-finals of the playoffs by the Vaughan Sun Devils, by a score of 2–0.

[5] After a contract disputes with the organization, he missed the entire 2004 season, due to Hamilton owning his player rights.

[9] In 2006, after an impressive season in Toronto he departed to Europe once more to sign with Lombard-Pápa TFC of the Borsodi Liga.

In the summer of 2006, he became the first Canadian-born player to be signed by Czech giants AC Sparta Prague.

[15] Simpson was reportedly linked Nottingham Forest of the English Championship Division after a brief stay at the club's grounds early May 2008.

On June 25, 2009, he played as part of the Zinedine Zidane squad in a charity match against the Canadian All-Stars.

In April 2011, he came out of retirement to sign with his home club Mississauga Eagles FC of the Canadian Soccer League, and was named the team captain.