Hydroxyl terminated liquid epoxidized natural rubber (HTLENR) was successfully synthesized via oxidative degradation of liquid epoxidized natural rubber (LENR) in the presence of cobalt (II) acetyl acetonate (CAA) as the oxidizing agent. The effect of reaction time on molecular weight, chemical structures and hydroxyl content of HTLENR were investigated. The weight average molecular weight (Mw) and polydispersity index (PDI) of the prepared HTLENR were determined using gel permeation chromatography (GPC). The result shows that as the reaction time increased, the Mw decreased indicating the occurrence of higher chain scission. It was found that the lowest Mw was achieved at 10 h reaction time where the Mw and Mn were 37,545 g/mol and 3,233 g/mol. The structural analysis and hydroxyl content of HTLENR on the other hand, were studied by using fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR). The presence of OH group was confirmed by FTIR analysis with the appearance of broad peak at 3,200 - 3,600 cm-1. Subsequently, NMR analysis also confirmed that the highest amount of hydroxyl content which is 7.56 % was achieved at the longest reaction time which is 10 h.