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[Display omitted] • Hydrothermal pretreatment is a sustainable approach for the recovery of XOS. • XOS and GOS of 23.7 and 18.3% respectively was obtained under best conditions. • Conduritol B epoxide served as inhibitor for controlled hydrolysis to get cellobiose. • After controlled hydrolysis 174 mg of cellobiose was obtained per gram of biomass. Globally, the demands for sustainably sourced functional foods like prebiotic oligosaccharides have been constantly increasing. This study assessed the potential of pineapple leaves (PL) as lignocellulosic feedstock for sustainable production of cellulose and hemicellulose-derived oligosaccharides through its hydrothermal pretreatment (HT) followed by controlled enzymatic hydrolysis. PL was subjected to HT at 160, 175, and 190 °C for 20, 30, 60, and 90 min without any catalyst for xylooligosaccharide (XOS) production, whereas, the resulting solid content after HT was subjected to controlled enzymatic hydrolysis by commercial cellulase using conduritol B epoxide (0.5–5 mM) for glucooligosaccharides (GOS) production. HT at 160 °C for 60 min resulted in maximum yield of XOS and GOS at 23.7 and 18.3 %, respectively, in the liquid phase. Controlled enzymatic hydrolysis of HT treated (160 °C) PL solids for 20 and 30 min yielded ∼ 174 mg cellobiose/g dry biomass within 24 h, indicating overall high oligosaccharide production. [ABSTRACT FROM AUTHOR]