This paper presents a new approach to estimate spatial Sun-Induced Fluorescence (SIF) using the empirical relationship between simulated Canopy Chlorophyll Concentration (CCC) and simulated SIF. PROSAIL model [PROpriétésSPECTrales (PROSPECT) and Scattering by Arbitrarily Inclined Leaves (SAIL) models] was used to simulate CCC. CCC maps were generated through an Automated Radiative Transfer Model Operator (ARTMO) using the PROSAIL model and Sentinel-2 Multi-Spectral Imager (MSI) imagery. The Soil Canopy Observation, Photochemistry, and Energy fluxes (SCOPE) model was used to simulate SIF emitted at 740 nm (SIF740), at 760 nm (SIF760), and top of canopy (SIFTOC) (640-850 nm). The SCOPE model, configured with the specification of the Sentinel-2 sensor, simulates SIF within the spectrum range of 640-850 nm. A non-linear logarithmic relationship (R2 > 0.9, p < 0.05) was observed between simulated SIF and simulated CCC. Simulated CCC was linearly related to observed CCC with R2 0.88, 0.92 and 0.89 and RMSE = 0.04, 0.17 and 0.09 gm/m2 at p < 0.05 for summer, post-monsoon and early winter respectively. Whereas, the simulated CCC did not capture the full range of CCC variability for the post-monsoon season. Simulated SIF (SIF760) was well correlated with SIF from Orbiting Carbon Observatory-2 (OCO-2) satellite with R2 0.68, 0.73 and 0.73 (RMSE = < 1 W/m2/sr/μm, p < 0.05) for the month of summer (April), pre-monsoon (May) and early winter season (November) respectively. Temporal SIFTOC effectively captured the seasonal variability associated with the phenology of deciduous tree species. Among various Sentinel-2 MSI derived VIs, Red Edge NDVI (RENDVI) exhibited maximum sensitivity with SIF (highest monthly average R2 > 0.6, p < 0.05). The spatial SIF would serve as an useful link between airborne /satellite derived SIF and in-situ fluorescence measurements to understand multiscale SIF variability of terrestrial vegetation.