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Tramadol (TRA) is a poorly biodegradable pharmaceutical, ubiquitously distributed in the aquatic environment. Herein, we present a thorough comparison of two conventional (UV and chlorination) and two advanced oxidative processes (UV-H2O2 and UV-chlorine), in terms of TRA removal efficiency and transformation products (TPs) formation. The performance of these processes was evaluated in different complexity water samples, previously adjusted at neutral pH. Using 1 mg L−1 as initial concentration of oxidant, UV-chlorine was the most effective process followed by UV-H2O2, direct photolysis and chlorination. The efficiency of the investigated treatments decreased for surface and wastewater samples compared to model solutions. Despite this limitation, the UV-chlorine treatment removed more than 70% of TRA measured in wastewater samples after 5 min of UV irradiation, in presence of 10 mg L−1 of chlorine. UV-chlorine involved additional degradation routes to those described for the rest of treatments, including the formation of tramadol-N-oxide, several chlorinated derivatives, and the volatile species chloroform, 1,1-dichloroacetone and anisole. Some of these specific TPs might pose a similar toxicity to that associated to the parent compound; however, their maximum formation yields remained below 2.5%, decreasing steady for reaction times longer than 5 min This study was supported through grants PGC2018-094613-B-I00 and ED431C 2021/06, funded by Spanish Government (Ministry of Science, Innovation and Universities) and Xunta de Galicia, respectively. Both projects are co-funded by the EU FEDER program. M.C.G. thanks a FPI fellowship to the Ministry of Science and Education (Spain) SI