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The chemical properties that serve as major determinants for the glycemic index (GI) of starchy food and recommended low-GI, carbohydrate-based foods have remained enigmatic. This present work performed a systematic assessment of linkages between chemical properties of foods and GI, and selected low-GI starchy foods. The data were sourced from literature published in various scientific journals. In total, 57 relevant studies and 936 data points were integrated into a database. Both in vitro and in vivo studies on GI values were included. The database was subsequently subjected to a meta-analysis. Meta-analysis from in vitro studies revealed that the two significant factors responsible for the GI of starchy foods were resistant starch and phenolic content (respectively, standardized mean difference (SMD): −2.52, 95% confidence interval (95%CI): −3.29 to −1.75, p (p-value) < 0.001; SMD: −0.72, 95%CI: −1.26 to −0.17, p = 0.005), while the lowest-GI crop type was legumes. Subgroup analysis restricted to the crop species with significant low GI found two crops, i.e., sorghum (SMD: −0.69, 95%CI: −2.33 to 0.96, p < 0.001) and red kidney bean (SMD: −0.39, 95%CI: −2.37 to 1.59, p = 0.001). Meta-analysis from in vivo studies revealed that the two significant factors responsible for the GI of starchy foods were flavonoid and phenolic content (respectively, SMD: −0.67, 95%CI: −0.87 to −0.47, p < 0.001; SMD: −0.63, 95%CI: −1.15 to −0.11, p = 0.009), while the lowest-GI crop type was fruit (banana). In conclusion, resistant starch and phenolic content may have a desirable impact on the GI of starchy food, while sorghum and red kidney bean are found …