Vitamin D3 stability has been a concern in the functional food industry. Protein conjugated with saccharides showed potential for an improvement in vitamin D3 stability. Novel and sustainable proteins, such as cricket protein, are of interest worldwide. Therefore, this research examined the utilization of cricket protein-fructooligosaccharide (FOS) conjugates formed through the Maillard reaction as a delivery system for vitamin D3 in an oil-in-water (O/W) emulsion. O/W emulsions with vitamin D3 stabilized by cricket protein powder (CP), cricket protein-FOS mixture (CPM), and cricket protein-FOS conjugates (CPF) with varying concentrations (0.3%, 0.5%, and 1.0% w/v). All emulsions had di-modal distributions with mean particle size diameters (D [4,3]) between 4.17 and 12.62 μm. The CPF emulsion had larger particle size diameters (8.46–12.62 μm) but less span value (3.26–4.76) when compared with CP and CPM (4.17–5.88 μm, 4.87–6.38). The storage stability of emulsions and vitamin D3 release (4 °C, 0–30 days) was improved by conjugated products. The CPF-stabilized vitamin D3 emulsions exhibited enhanced vitamin D3 bioaccessibility (37–54%), surpassing that of CP (27–34%) and CPM (32–37%). Furthermore, CPF showed superior vitamin D3 stability during in vitro gastrointestinal digestion. The concentration required for 50% inhibition of cell viability of CP, CPM, CPF, and CPF-vitamin D3 emulsion was 0.643, 0.552, 0.474, and 0.229 mg/mL, respectively, indicating low cytotoxic activity. These findings validate the effectiveness of cricket protein-FOS conjugates, particularly at a 1% (w/v) concentration, in improving the release of vitamin D3 in emulsion-based delivery systems and their potential for fortifying functional food products.