African swine fever (ASF) is a severe, globally important disease in domestic and wild pigs. The testing of alternative transmission routes has proven that the ASF virus (ASFV) can be efficiently transmitted to sows via semen from infected boars through artificial insemination. Boars intramuscularly inoculated with the ASFV strain “Estonia 2014” showed grossly and microscopically visible changes in the testis, epididymis, prostate, and vesicular gland. The gross lesions included hemorrhages on the scrotum, testicular membranes, and parenchyma; edema; hydroceles; and proliferations of the tunica vaginalis. Histopathologically, vasculitis and perivasculitis was detected in the testis and epididymis. Subacutely infected animals further revealed a degeneration of the testicular and epididymal tubules, pointing to the destruction of the blood–testis and blood–epididymis barriers upon disease progression. This was confirmed by evidence of semen round cells and sperm abnormalities at later time points after the infection. The histopathology was associated with the presence of viral DNA and the infectious virus, and in a limited amount with viral antigens. In most scenarios, the impact of these changes on the reproductive performance and long-term persistence of the virus is probably negligible due to the culling of the animals. However, under backyard conditions and in wild boar populations, infected males will remain in the population and the long-term fate should be further evaluated.