[1] He represented the Republic of Macedonia in two editions of the Olympic Games (2000 and 2004), and held five Macedonian records in the butterfly (50 and 100 m) and individual medley (100 and 200 m).

He cleared FINA B-standard entry times of 55.23 (100 m butterfly) and 2:07.38 (200 m individual medley) from the World Championships in Barcelona, Spain.

[4][5] In the 200 m individual medley, Miladinovski challenged seven other swimmers in heat two, including Olympic veterans Orel Oral of Turkey and Oleg Pukhnatiy of Uzbekistan.

After concluding his swimming career he continued working as an educator in international schools around Asia and the Middle East.

His next station after Dubai was Wellington College International Shanghai where he worked as Aquatics Director for four years.