This article focuses on the role that oxidative stress plays in chronic prostatitis, not only with respect to the known impact on symptoms and fertility but also especially in relation to possible prostate cancer development. Prostatitis is the most common urologic disease in adult males younger than 50 years and the third most common urologic diagnosis in males older than 50 years. If the germ-causing acute prostatitis is not eliminated, the inflammatory process becomes chronic. Persistent inflammation causes ongoing production of large quantities of pro-inflammatory cytokines and both oxygen and nitrogen reactive species, with consequent activation of transcription factor nuclear factor-kappa B (NF-κB) and genes encoding for further production of pro-inflammatory cytokines, chemotactic factors, and growth factors. Confirming the role of oxidative stress in chronic prostatitis, several studies have demonstrated the presence of oxidative stress markers in the genital secretions of patients suffering from the disease. Antioxidants can therefore play an essential role in the treatment of chronic bacterial and non-bacterial prostatitis; in the case of bacterial inflammation, they can be associated with antibiotic therapy. Moreover, due to their anti-inflammatory properties, antioxidants hinder the progression of inflammation and the possible development of prostate cancer.