The assessment and assurance of the quality attributes of dates is a key factor in increasing the competitiveness and consumer acceptance of this fruit. The increasing demand for date fruits requires a rapid and automated method for monitoring and analyzing the quality attributes of date fruits to replace the conventional methods used by inspection which limits the production and involves human errors. Moisture content (MC), dry matter content (DMC), and firmness (F) are three important quality attributes for two date cultivars (Khalas and Sukkari) that have been inspected using the hyperspectral imaging (HSI) technique based on the reflectance mode. Images of intact date fruits at the maturity stage Tamr were obtained within the wavelength range of 950–1750 nm. Monitoring and assessment of MC, DMC, and F [first maximum rupture force (MF, N)] were performed using a partial least squares regression model. Accurate prediction models were attained. The results highlight that the coefficients of determination (R2Prediction) are estimated to be 0.91 and 0.89 for MC, DMC, and F (N) with the lowest values of the standard error of prediction (SEP) equal to 0.82, 0.81 (%), and 4.12 (N), respectively, and the residual predictive deviation (RPD) values were 3.65, 3.69, and 3.42 for MC, DMC, and F (N), respectively. The results obtained from this preliminary study indicate the great potential of applying HSI for the assessment of physical, chemical, and sensory quality attributes of date fruits overall in the five maturity stages.