Cocoa is a major dietary source of polyphenols, including flavanols, which have been associated with reduced blood pressure (BP). While earlier systematic reviews and meta-analyses have shown significant effects of cocoa consumption on systolic BP, limitations include small sample sizes and study heterogeneity. Questions regarding food matrix and dose of polyphenols, flavanols, or epicatechins remain. This systematic review and meta-analysis aimed to investigate the effects of ≥2 weeks of cocoa consumption as a beverage or dark chocolate in those with normal or elevated (< or ≥130 mmHg) systolic BP measured in the fasted state or over 24-h. A systematic search conducted on PubMed and Cochrane Library databases up to 26 February 2022 yielded 31 suitable articles. Independent of baseline BP, cocoa consumption for ≥2 weeks was associated with reductions in systolic and diastolic BP (p < 0.05, all). Compared with cocoa, chocolate lowered the weighted mean of resting systolic BP (−3.94 mmHg, 95% CI [−5.71, −2.18]) more than cocoa beverage (−1.54 mmHg, 95% CI [−3.08, 0.01]). When the daily dose of flavanols was ≥900 mg or of epicatechin ≥100 mg, the effect was greater. Future, adequately powered studies are required to determine the optimal dose for a clinically significant effect.