on 13 december 2003, aged 16, kaluđerović made his senior debut for ofk beograd under manager stevica kuzmanovski, coming on as an injury-time substitute for hristijan kirovski in a 1–1 away league draw against budućnost banatski dvor. he spent the majority of the following three seasons on loan to various clubs, most notably spartak subotica in the serbian first league. in the 2009 winter transfer window, kaluđerović moved from ofk beograd to fellow serbian superliga club rad.