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This paper examines the use of simulated and measured canopy reflectance for chlorophyll estimation over crop canopies. Field spectral measurements were collected over corn and wheat canopies in different intensive field campaigns organized during the growing seasons of 2004 and 2005. They were used to test and evaluate several combined indices for chlorophyll determination using hyperspectral imagery (Compact Airborne Spectrographic Imager). Several index combinations were investigated using both PROSPECT-SAILH canopy simulated spectra and field-measured reflectances. The relationships between leaf chlorophyll content and combined optical indices have shown similar trends for both PROSPECT-SAILH simulated data and ground-measured data sets, which indicates that both spectral measurements and radiative transfer models hold comparable potential for the quantitative retrieval of crop foliar pigments. The data set used has shown that crop type had a clear influence on the establishment of predictive equations as well as on their validation. In addition to generating different predictive equations, corn and wheat data yielded contrasting agreement between estimated and measured chlorophyll contents even for the same predictive algorithm. Among the set of indices tested in this paper, index combinations like modified chlorophyll absorption ratio index/optimized soil-adjusted vegetation index (OSAVI), triangular chlorophyll index/OSAVI, moderate resolution imaging spectrometer terrestrial chlorophyll index/improved soil-adjusted vegetation index (MSAVI), and red-edge model/MSAVI seem to be relatively consistent and more stable as estimators of crop chlorophyll content.