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Simple Summary: The roe deer is a small wild ruminant, very common in Europe and Asia; adult specimens are sexually active only during summer, in very short timeframes. Peculiarly, males, also known as bucks, produce spermatozoa only in this period, with a subsequent morph-functional testicular involution. In seasonal breeders, melatonin plays a pivotal role by converting light information and controlling the testicular hormonal function and, recently, its local production within testes has been described in other species. The aim of the present work was to study testicular melatonin and its synthesis pathway in roe deer during the pre-rut (June–July) and post-rut (August–September) periods, and correlate it with morph-functional testicular changes. Samples were opportunistically obtained from hunted specimens according to the local hunting calendar. The results also seem to suggest a local melatonin production in this species, but no correlations with testicular involution parameters were highlighted, probably due to the very short sampling timeframe. More studies are necessary to understand the role of melatonin in the testicular cycle and provide more information regarding the interesting reproductive physiology of this species. Roe deer are seasonal breeders with a complete yearly testicular cycle. The peak in reproductive activity is recorded during summer, the rutting period, with the highest levels of androgens and testicular weight. Melatonin plays a pivotal role in seasonal breeders by stimulating the hypothalamus–pituitary–gonads axis and acting locally; in different species, its synthesis within testes has been reported. The aim of this study was to evaluate the physiological melatonin pattern within roe deer testes by comparing data obtained from animals sampled during pre- and post-rut periods. Melatonin was quantified in testicular parenchyma, along with the genetic expression of enzymes involved in its local synthesis (AANAT and ASMT) and function (UCP1). Melatonin receptors, MT1-2, were quantified both at protein and gene expression levels. Finally, to assess changes in reproductive hormonal profiles, testicular dehydroepiandrosterone (DHEA) was quantified and used for a correlation analysis. Melatonin and AANAT were detected in all samples, without significant differences between pre- and post-rut periods. Despite DHEA levels confirming testicular involution during the post-rut period, no correlations appeared between such involution and melatonin pathways. This study represents the first report regarding melatonin synthesis in roe deer testes, opening the way for future prospective studies in the physiology of this species. [ABSTRACT FROM AUTHOR]