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Background: There is significant pathogenic and epidemiological overlap between diabetes and obstructive sleep apnea (OSA). This systematic review aimed to ascertain the association between OSA and cardiovascular disease (CVD) in a diabetic population. Methods: The study protocol was registered with PROSPERO (CRD42023404126). On 15 July 2023, a comprehensive search of the literature was performed in PubMed, EBSCO, Scopus, ProQuest, and Web of Science, using keywords and synonyms of OSA, diabetes, and CVD, coupled with specific terms for different CVDs. Only observational studies that reported CVD events in diabetics (with and without OSA) were included. The quality of the studies included in the analysis was assessed using the Newcastle–Ottawa Scale. Results: In the primary literature search, 8795 studies were identified, of which 9 met the inclusion criteria and included 17,796 participants. Eight studies were eligible for meta-analysis, and a pooled risk ratio (RR) of 1.29 (95% CI = 0.91–1.83) was found for developing CVD in diabetics with OSA at a 95% prediction interval of 0.30–5.60. The included studies showed significant heterogeneity with an I2 value of 91%. Conclusion: These findings show the possible association between OSA and diabetes and their impact on CVDs. Identifying and managing OSA in individuals with diabetes at an early phase could potentially reduce the risk of CVDs and its related complications.