Dragoljub Miloševic (8 November 1929 – 2 October 2005) was a Serbian footballer and football manager.
He played for VSK, OFK Napred, Buducnost Valjevo, Jedinstvo Zemun, Red Star Belgrade, Macva Šabac and Metalac Valjevo.
He coached Buducnost Valjevo, Metalac Valjevo, Radnicki Niš, Sloboda Titovo Užice, Vojvodina, Celik Zenica, Valencia CF, Olimpija Ljubljana, Buducnost Titograd, Napredak Kruševac, Cádiz CF and CD Tenerife.