[2] Trichkovski spent the 2009–10 season on loan at Enosis Neon Paralimni where he scored 8 goals in 29 appearances and caught the eye of a successful club in Cyprus, APOEL, who agreed in principle to a three-year deal with Trickovski in May 2010.

[3] In December 2010, the Belgian club Lokeren made an official offer of €1.2 million for Trickovski but APOEL rejected it.

[5] In June 2012, Trichkovski moved to Belgian side Club Brugge for an undisclosed fee, reportedly in the region of €1.2 million.

On 1 August 2019, he scored a career-high four goals in a 4–0 away win over Bulgarian club Levski Sofia in a second qualifying round UEFA Europa League match.

Trichkovski was a member of the Macedonia U21[citation needed] before he was called up in February 2008 for the senior squad to face Serbia in a friendly,[15] but he was forced to withdraw due to injury.