Food matrices are becoming increasingly complex with the impregnation of phytonutrients with health-beneficial pharmacological effects. Herein, we report the preparation, characterization, and functional application of soluble and stable microspheres of trans-resveratrol (t-RES) developed through a water-based green process involving cyclodextrin (CD) and fenugreek galactomannan (FG). Spectroscopic and thermodynamic calculations identified γ-CD as the best CD to form a stable cyclodextrin-resveratrol inclusion complex (CD-R, 49-fold enhanced solubility); however, it exhibited a burst release profile. The sustained release of resveratrol was achieved by further encapsulating the inclusion complex within the fenugreek galactomannan hydrogel scaffold by a gel-phase dispersion process, resulting in an amorphous powder (FG-CD-R) as evident from powder X-ray diffraction (PXRD), differential scanning calorimetry (DSC), and scanning electron microscopy (SEM) studies. Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR) studies confirmed the formation of the inclusion complex with no chemical alterations. When dissolved in water, FG-CD-R swelled and released stable cuboid structures with an average particle size of 500 ± 53 nm with a zeta potential of -52 ± 5.3 mV. FG-CD-R demonstrated a sustained-release profile upon in vitro release studies. Accelerated study demonstrated its stability for a shelf-life of two years. Further it was shown to be suitable for the preparation of transparent gummies with improved sensory attributes compared to unformulated t-RES. In summary, FG-CD-R is simple to prepare and easily scalable, providing a sustained-release t-RES with a natural, food-grade, and clean label status (non-genetically modified, allergen-free, vegan, and free from residual solvents) for nutritional applications.