Human corticosteroid-binding globulin (hCBG) is a heavily N-glycosylated protein that transports cortisol in plasma. We previously demonstrated that Asn347-glycans positioned on the exposed reactive centre loop (RCL) of hCBG impact the release of cortisol by modulating the neutrophil elastase (NE)-mediated RCL cleavage at inflammatory sites. However, a comprehensive structure-function characterisation of the RCL glycosylation is still required to unravel the molecular mechanisms underpinning cortisol delivery to inflamed tissues. To this end, we have performed a deep RCL-centric glycoprofiling of hCBG isolated from healthy sera using glycomics and glycoproteomics. Glycoprofiling and longitudinal NE-centric cleavage experiments were also performed on HEK293-derived recombinant human CBG (rhCBG) to study how the RCL glycosylation impacts the NE-mediated cleavage process and cortisol release. Surprisingly, the hCBG glycoprofiling revealed a hitherto unknown presence of RCL O-glycosylation. Two core 1-type O-glycans (NeuAc1-2Gal1GalNAc1) were found to occupy four O-glycosylation sites within the RCL, including the strategically-positioned Thr345 site proximal to the Val344-Thr345 cleavage site targeted by NE. Interestingly, some hCBG glycoforms displayed an intriguing N- and O-glycan co-occurrence involving the co-occupancy of Asn347 and either Thr338 or Thr342 suggesting a crosstalk between N- and O-glycosylation on the RCL. In contrast, rhCBG glycoprofiling revealed high levels of core 1/2-type O-glycosylation (NeuAc1-2Gal1-2GalNAc1-2) at the Thr345 site and negligible glycosylation of other potential RCL sites. Notably, longitudinal NE-centric cleavage experiments demonstrated that sialo-, asialo-, and agalacto-glycans decorating Thr345 of rhCBG strongly protect against NE proteolysis, which was supported by molecular dynamics simulations that substantiated that a Thr345-positioned O-GalNAc residue can protect against NE interactions and, in turn, block cortisol release from CBG. In conclusion, we are the first to report on strategically-positioned and functionally-relevant N- and O-glycans occupying the RCL of hCBG. These findings improve our understanding of the molecular mechanisms governing the timely and tissue-specific delivery of cortisol to inflammatory sites.