Objective: To isolate and investigate antioxidant and α-glucosidase inhibitor compounds in the leaves of Quercus gilva Blume (Q. gilva). Methods: Dry leaves of Q. gilva were extracted with methanol and the methanolic extract was further separated by silica gel column chromatography using several solvents with increasing polarity. The antioxidant activities of the isolated compounds were evaluated using various in vitro assays: 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity, hydrogen peroxide radical scavenging activity, β-carotene bleaching assay, and reducing power assay. The α-glucosidase inhibitory assay was conducted against α-glucosidase from Saccharomyces cerevisiae. Results: Three compounds were isolated and their structures were identified as catechin (1), epicatechin (2), and tiliroside (3) using an instrumental analysis. Compound 2 had higher antioxidant activity with inhibitory concentrations (IC50) of (22.55 ± 2.23) μmol/L than that of quercetin, which was used as the standard, with an IC50 of (28.08 ± 2.39) μmol/L, followed by compound 1 with IC50 of (40.86 ± 3.45) μmol/L. On the other hand, compound 3 had the lowest antioxidant activity with an IC50 of (160.24 ± 8.15) μmol/L. However, compound 3 had the highest α-glucosidase inhibitory activity with an IC50 of (28.36 ± 0.11) μmol/L, followed by compounds 1 and 2 with (168.60 ± 5.15) and (920.60 ± 10.10) μmol/L, respectively. Conclusions: The results obtained for the antioxidant activities and α-glucosidase inhibitory activities in a methanolic extract from the leaves of Q. gilva confirmed the potential of this plant as a source of natural antioxidants and antidiabetic medicine.