Prostatitis-like syndromes are high prevalent health problems and frequently considered by patients and physicians as strictly correlated to sports causing perineal compression. These syndromes and their relationships with sporting activities have been discussed in this report. We reviewed peer-reviewed scientific articles published by May 2009 and searched according to the following term selection: prostatitis, pudendal nerve, sport, cycling. Chronic prostatitis/chronic pelvic pain syndrome (CP/CPPS) is a major healthcare burden heavily affecting patients' Quality of Life. No clear evidence of any direct etiologic relationship has been found in literature between prostatitis, either bacterial or non-bacterial, and sports activities. On the other hand, some types of sport causing perineal compression, such as cycling, can exacerbate symptoms of acute and chronic prostatitis; a temporary sport discontinuation is justified in these patients. CP/CPPS may be often caused by pudendal nerve entrapment (PNE). Prostatitis-like urogenital neuropathic pain together with voiding and sexual dysfunctions are the hallmark of PNE. A common feature is that flexion activities of the hip, such as climbing, squatting, cycling provoke or worsen urogenital pain or pelvic pain. Many of the patients with PNE are cyclists, played American football, lifted weights, or wrestled as teenagers and young adults. PNE represents the most common bicycling associated urogenital problems. Overall, studies show that no causal relationship has been demonstrated between prostatitis and sporting activities. Conversely, urologists should be aware that sports involving vigorous hip flexion activities or prolonged perineal compression are a potential and not an infrequent cause of uroandrological symptoms caused by pudendal nerve entrapment.