Saba banana, a popular fruit crop grown in Southeast Asia, is an economical source of a variety of beneficial agents. This study examined the variations in total phenolic, flavonoid, and antioxidant activities of five maturity stages of Saba banana, and their changes during simulated in vitro gastrointestinal digestion as affected by varying structural compositions. Antioxidant activities were evaluated using ferric reducing antioxidant power (FRAP), metal ion chelating (MIC) activity, and 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. Results of DPPH and ABTS were compared in terms of TEAC (Trolox Equivalent Antioxidant Capacity) and VCEAC (Vitamin C Equivalent Antioxidant Capacity) values. Bio-properties were found to be highest in mature green stage with values slightly decreased as ripening proceeded. Simulated digestion showed a continuous increase in total phenolic with comparatively faster release in structure-less state (slurry) than samples with intact structure (cut). The trend of antioxidant activities was increased in the gastric phase and then decreased at the onset of intestinal phase, except for MIC which showed a reverse effect. Our study indicated that the bio-properties of Saba banana were affected by maturity and modifications in its physical structure and composition could influence the release behaviors of food components during simulated digestion.