Born in Aranđelovac, Milojević joined the youth system of Red Star Belgrade in 1986, before making his senior debuts with Bečej.

[1] He also played for Kalamata, again with Muf, before returning to his homeland and joining his parent club Red Star Belgrade in early 1996.

In June 2011, Milojević was appointed manager of Serbian SuperLiga side Javor Ivanjica, but left the club after three months.

Two years later, Milojević won his first trophy as a manager when Čukarički defeated Partizan 1–0 in the 2014–15 Serbian Cup final.

[9] In the 2019–20 season, Milojević again managed to reach the UEFA Champions League group stage after defeating some tough opponents in the likes of København and Young Boys.

On 19 December 2019, Milojevic announced his resignation as manager of Red Star Belgrade even though the team is 11 points clear in the Serbian league.

On 31 August 2023, Milojević became the manager of another Cypriot club, Apollon Limassol..On December 5, Milojevic resigned as coach due to poor results.