This work analyzes the influence of whitening a greenhouse roof on the microclimate and yield of a tomato crop. In the west sectors of two multi-span greenhouses, a whitening concentration of 0.250 kg L−1 was used as a control. In an autumn–winter cycle, a lower (0.125 kg L−1) and an increased (0.500 kg L−1) concentration were used in the east sectors of greenhouses 1 and 2. In a spring–summer cycle, the whitening concentrations in the east were varied depending on outside temperature. The effect of whitening on photosynthetic activity, production, plants’ morphological parameters, and the quality of the fruits were also analyzed. To evaluate the effect on microclimate, solar and photosynthetically active (PAR) radiations, air and soil temperatures, and heat flux in the soil were measured in greenhouse 1. Results show that excessive whitening leads to reductions of inside PAR radiation that decreases photosynthesis and crop yield. A whitening concentration of 0.500 kg L−1 is proposed at the beginning of the autumn–winter crop cycle, washing the cover when inside temperature drops to 35 °C. At the end of the spring–summer cycle, a concentration of 0.125 kg L−1 is recommended when inside temperature increases to 35 °C.