Aside from a few years in the amateur Dutch leagues, Caanen never played professional football. He got his start as a youth manager in his hometown while also working as a salesman for the local Toyota dealership.
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 (UEFA Champions League or UEFA Cup). 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 Division Hapoel 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.