Phytophthora fruit rot, caused by Phytophthora capsici, is a major constraint to cucurbit production for the processing industry in Michigan. Age-related resistance to Phytophthora fruit rot has been identified in pepper and some cucurbit fruit. In this study, ‘Dickenson Field’ processing pumpkin (Cucurbita moschata) and ‘Golden Delicious’ winter squash (C. maxima) were evaluated for age-related resistance to Phytophthora fruit rot. Hand-pollinated fruit were harvested 3, 7, 10, 14, 21, 28, 42, or 56 days post pollination (dpp), and inoculated with P. capsici isolate 12889. Susceptibility to Phytophthora fruit rot decreased with fruit age in Dickenson Field processing pumpkin, whereas Golden Delicious winter squash remained susceptible to fruit rot even as fruit reached full physiological maturity. Less than 15% of Dickenson Field fruit 21 dpp or older became diseased. Conversely, about 80% of Golden Delicious fruit 21 dpp or older became diseased. Lesion diameter and pathogen growth density ratings differed significantly (P < 0.0001) among fruit ages for both cultivars, and were negatively correlated (ρ = –0.37 to –0.87) with fruit age. Lesion diameter and pathogen growth were generally greater on younger fruit than older fruit. Lesion diameter was greatest on 7- and 10-dpp-old fruit of Dickenson Field and Golden Delicious, respectively. Pathogen growth density ratings were greatest on 3-dpp-old fruit of both cultivars. Several morphological and physiological changes were observed as fruit matured. Soluble solids content and exocarp firmness of both cultivars increased with fruit age. Lesion diameter and pathogen growth density ratings were negatively correlated (ρ = –0.29 to –0.73) with soluble solids content and exocarp firmness.