Background: Retirement from elite sport participation is associated with decreased physical activity, depression, obesity, and ischemic heart disease. Although engagement in physical activity through sport is recognized as cardioprotective, an estimated one-quarter of deaths in American football players are associated with cardiovascular disease (CVD), predominately in players classified as obese. Purpose: To systematically investigate the cardiovascular health profile of retired field-based athletes. Study Design: Systematic review; Level of evidence, 4. Methods: This review was conducted and reported in accordance with the PRISMA (Preferred Reporting Items for Systematic Reviews and Meta-Analyses) guidelines and preregistered with PROSPERO. Four databases (PubMed, CINAHL, Embase, and Web of Science) were systematically searched from inception to October 2018 using MeSH terms and keywords. Inclusion criteria were retired field-based athletes, age >18 years, and at least 1 CVD risk factor according to the European Society of Cardiology and the American Heart Association. Review articles were not included. Control groups were not required for inclusion, but when available, an analysis was included. Eligible articles were extracted using Covidence. Methodological quality was assessed independently by 2 reviewers using the AXIS tool. The accuracy of individual study estimates was analyzed using a random-effects meta-analysis. Results: This review yielded 13 studies. A total of 4350 male retired field-based athletes from 2 sports (football and soccer; age range, 42.2-66 years) were included. Eight studies compared retired athletes with control groups. Retired athletes had elevated systolic blood pressure in 4 of 6 studies; approximately 50% of studies found greater high-density lipoprotein, approximately 80% found lower triglyceride levels, and all studies found greater low-density lipoprotein for retired athletes compared with controls. The prevalence and severity of coronary artery calcium and carotid artery plaque were similar to controls. Retired linemen had double the prevalence of cardiometabolic syndrome compared with nonlinemen. Conclusion: The overall findings were mixed. Inconsistencies in the reporting of CVD risk factors and methodological biases reduced the study quality. Retired athletes had a comparable CVD risk profile with the general population. Retired athletes with an elevated body mass index had an increased prevalence and severity of risk factors. Significant gaps remain in understanding the long-term cardiovascular effects of elite athleticism.