Aside from a few years in the amateur Dutch leagues, Caanen never played professional football. He got his start as a manager in his hometown club :nl:FC Geleen Zuid|FC Geleen Zuid while also working as a salesman for the localToyota dealership. After two years with FC Geleen Zuid he started to work as the youth manager of Roda JC.
In January 2004 he made his way to the Ukrainian Premier League as he signed as manager of Metalurh Donetsk. He left the club at the end of the season.
When Arcadi Gaydamak bought the Israeli football club, Beitar Jerusalem, he looked for someone who would be able to give the club a look over and see what changes needed to be made. Caanen was brought in and after a short time was given the reigns of the club after Eli Ohana, stepped down from the manager position. Continuing with the same squad as Ohana had, Kaanen was able to produce good results making him a 'lifeline' to hopes in the club that they would be able to qualify for a continental competition. When Luis Fernandez was appointed general manager over Caanen, there was a lot of friction over Caanen's qualifications to manage a club looking to become a European power. Caanen was soon fired but made a lasting impression on the Israeli public that would later pay dividends.
When the Maccabi Tel Aviv boardroom had enough of the poor results on the pitch during the club's 100 year anniversary, it was evident that Israeli manager Nir Klinger was on his way out. Caanen was appointed interim manager. Despite two big money "name" signings the team were a disaster typified by a 4-0 loss to Second DivisionHapoel Akko in the Cup.
In June 2009 Caanen signed a contract as the coach of the Maltese club Valletta. "The objective in the country is the championship and the connection to get to Europe", said Caanen in Limburg. He took Jordi Cruyff with him to the island as an assistant coach and player. The two worked before together at Metalurh Donetsk.
In summer of 2010 Jordi Cruyff announced his retirement from professional football and joined AEK Larnaca as Director of Football. He signed Caanen as head coach, and the pair worked to establish the team as a new football powerhouse in Cyprus.
Veria
In September 1, 2013 the Greek superleague side Veria F.C. announced that Caanen was appointed as the team coach. After a few weeks he quit.