Technical Abstract: In peanut, the mechanism of resistance to fungal infection is reportedly due to the synthesis of stilbene phytoalexins, which are antibiotic, low molecular weight metabolites. The phytoalexin-associated response of different peanut genotypes to exogenous invasion in the field has not been investigated and may be useful for breeding resistant peanut cultivars. Five peanut genotypes, Georgia Green, Tifton 8, C-99R, GK-7 high oleic, and MARC I, that differ in resistance to major peanut diseases were investigated for their ability to produce phytoalexins under field conditions in Southwest Georgia in 2001 and 2002. Five known peanut phytoalexins, trans-resveratrol, trans-arachidin-1, trans-arachidin-2, trans-arachidin-3, and trans-3-isopentadienyl-4,3',5'-trihydroxystilbene (IPD), were quantitated. The phytoalexins were measured in peanuts of different pod maturity (yellow, orange, brown, and black) with or without insect pod damage (externally scarified or penetrated). Kernels from insect-damaged pods of C-99R and Tifton 8 genotypes had significantly higher concentrations of phytoalexins than other genotypes. The same genotypes were the most resistant to tomato spotted wilt virus and late leafspot, while MARC I, which is highly susceptible to these diseases, produced very low concentrations of phytoalexins. However, there was no significant difference in phytoalexin production by undamaged peanut pods of all tested genotypes. Trans-arachidin-3 and trans-resveratrol were the major phytoalexins produced by insect-damaged peanuts. In damaged seeds the concentrations of trans-IPD were significantly higher in Tifton 8 compared to other genotypes. There was an association between total phytoalexin production and published genotype resistance to major peanut diseases. Stilbene phytoalexins may be considered potential chemical markers in breeding programs for disease-resistant peanuts.