The 44-year-old was appointed in October 2015, when Ljubinko Drulovic left to take over at Serbian giants Partizan Belgrade.
Angelovski enjoyed great success in his first role with Rabotnicki, winning the league and cup double at the end of his first season in charge.
He followed that up with another victory in the Macedonian Football Cup a year later, beating Teteks 2-1 in the final.
He was the outstanding candidate to replace Drulovic when the time came, and made history by guiding North Macedonia to their first major international tournament.
After finishing second-bottom of their qualifying group for the last World Cup, few predicted seeing Angelovski’s side challenge for a spot at Euro 2020.
North Macedonia beat Kosovo and then Georgia, thanks to Goran Pandev’s decisive goal, to secure their passage to a much-anticipated tournament debut.
Little is expected of the Eastern European minnows, but they proved that they have the capacity to spring a surprise by winning 2-1 away to Germany in March.
Pandev, the team’s captain, most capped player and leading scorer, was on the mark again and he will be crucial to how his country fare this summer.
Aside from the 37-year-old attacker, Angelovski’s squad is low on star quality, but does include Leeds United’s Ezgjan Alioski, who enjoyed an excellent season in the Premier League.
Thank you for reading 5 articles this month* Join now for unlimited access
Enjoy your first month for just £1 / $1 / €1
*Read 5 free articles per month without a subscription
Join now for unlimited access
Try first month for just £1 / $1 / €1