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This study aims to comprehensively explore the phytoconstituents as well as investigate the different biological activities of <i>Chasmanthe aethiopica</i> (Iridaceae) for the first time. Metabolic profiling of the leaf methanol extract of <i>C. aethiopica</i> (CAL) was carried out using HPLC-PDA-ESI-MS/MS. Twenty-nine compounds were annotated belonging to various phytochemical classes including organic acids, cinnamic acid derivatives, flavonoids, isoflavonoids, and fatty acids. Myricetin-3-<i>O</i>-rhamnoside was the major compound identified. GLC/MS analysis of the <i>n</i>-hexane fraction (CAL-A) resulted in the identification of 45 compounds with palmitic acid (16.08%) and methyl hexadecanoic acid ester (11.91%) representing the major constituents. CAL-A exhibited a potent anti-allergic activity as evidenced by its potent inhibition of <i>β</i>-hexosaminidase release triggered by A23187 and IgE by 72.7% and 48.7%, respectively. Results were comparable to that of dexamethasone (10 nM) in the A23187 degranulation assay showing 80.7% inhibition for <i>β</i>-hexosaminidase release. Both the <i>n</i>-hexane (CAL-A) and dichloromethane (CAL-B) fractions exhibited potent anti-inflammatory activity manifested by the significant inhibition of superoxide anion generation and prohibition of elastase release. CAL showed anti-hyperglycemic activity in vivo using streptozotocin-induced diabetic rat model by reducing fasting blood glucose levels (FBG) by 53.44% as compared with STZ-treated rats along with a substantial increase in serum insulin by 22.22%. Molecular modeling studies indicated that dicaffeoylquinic acid showed the highest fitting with free binding energies (∆G) of −47.24 and −60.50 Kcal/mol for human <i>α</i>-amylase and <i>α</i>-glucosidase, respectively confirming its anti-hyperglycemic activity. Thus, <i>C. aethiopica</i> leaf extract could serve as an effective antioxidant natural remedy combating inflammation, allergy, and hyperglycemia.