The degradation of epoxidized natural rubber (ENR-50) and liquid epoxidized natural rubber (LENR) was done via oxidative degradation method for the production of hydroxyl terminated epoxidized natural rubber (HTENR) and hydroxyl terminated liquid epoxidized natural rubber (HTLENR) has been analysed. Cobalt (II) acetylacetonate (CAA) were used as an oxidizing agent for chain scission reaction at temperature 60 C in the presence of ethanol. The reaction temperature was fixed at 60 C meanwhile reaction time and the amount of CAA were varied according to the reaction formulation. The HTENR and HTLENR obtained have been characterized using Gel Permeation Chromatography (GPC), Fourier Transform Infrared (FTIR) and Nuclear Magnetic Resonance (NMR). GPC were used to determine the molecular weight before and after the oxidative degradation of respected HTENR and HTLENR were compared with ENR-50 and LENR. The lowest Mn and Mw of HTLENR that were obtained from the oxidative degradation method were found to be 5,163 g/mol and 58,087 g/mol. The appearances of OH end groups were verified by FTIR and NMR analyses to validate the position of each OH functional groups. FTIR analysis confirmed that HTENR and HTLENR contained OH group with the appearance of a broad peak around 3,400 cm-1 to 3,550 cm-1 after the reaction. The presence of OH end groups was verified by NMR analysis with the appearance at 3.39 ppm and 3.66 ppm, corresponding to methylene proton adjacent to hydroxyl group in HOCH2CH2CH2 and methane proton adjacent to OH group in CH2CH2CH(OH)CH3.