Introduction: Prostate cancer (PCa) is a heterogenous disease with multiple etiological factors playing a role in its development. Recently, chronic and systemic inflammatory conditions such as inflammatory bowel disease were identified as key risk factors influencing its development. The study aimed to evaluate the relationship between diverticular disease (DD) (local and acute inflammation) and PCa. Methods: Hypertensive patients with DD and hypertensive controls were identified between 1995 and 2010 from the Statewide Planning and Research Cooperative System database. Cohorts were queried for PCa incidence through 2015. Univariable and multivariable logistic regression analyses were used for determining independent predictors of PCa diagnosis. Results: A total of 51,353 patients with DD and 111,541 controls were identified. In all, 6.26% of DD developed PCa, and 3.71% of controls developed PCa (p < 0.01). DD was a significant risk factor for PCa (OR: 1.27 CI: 1.19–1.34, p < 0.01). On subgroup analysis, the patients diagnosed with DD <50 years old had an OR of 3.39 for PCa (CI: 2.52–4.56, p < 0.01), age 50–59 had an OR of 2.12 (CI: 1.86–2.15, p < 0.01), and age 60–69 had an OR of 1.20 (CI: 1.10–1.31, p < 0.01). Finally, age and race stratification showed that white patients <50 had an OR of 2.56 (CI: 1.75–3.76, p < 0.01), while black patients <50 had an OR of 3.98 (CI: 2.61–6.07, p < 0.01). The trend in differing odds between these populations was the same for age groups 50–59 and 60–69. Conclusion: Our analysis shows that DD is associated with diagnosis of PCa in hypertensive men. Importantly, the earlier the diagnosis of DD, the higher the odds for development of PCa, particularly in black men.