Transfer of herbicide resistance genes between crops and weeds is relatively well documented; however, far less information exists for weed-to-weed interactions. The hybridization between the weedy diploids Conyza canadensis (2n = 18) and C. ramosissima (2n = 18) was investigated by monitoring transmission of the allele conferring resistance to N-phosphonomethyl glycine (glyphosate). In a multivariate quantitative trait analysis, we described the phylogenic relationship of the plants, whereas we tested seed viability to assess potential postzygotic reproductive barriers (PZRB) thus affecting the potential establishment of hybrid populations in the wild. When inflorescences were allowed to interact freely, approximately 3% of C. ramosissima or C. canadensis ova were fertilized by pollen of the opposing species and produced viable seeds; >95% of the ova were fertilized under no-pollen competition conditions (emasculation). The interspecific Conyza hybrid ( ) demonstrated an intermediate phenotype between the parents but superior resistance to glyphosate compared to the resistant C. canadensis parent. Inheritance of glyphosate resistance in the selfed ( ) followed the partially dominant nuclear, single-gene model; backcrosses confirmed successful introgression of the resistance allele to either parent. Negligible PZRB were observed in the hybrid progenies, confirming fertility of the C. canadensis × C. ramosissima nothotaxa. The implications of introgressive hybridization for herbicide resistance management and taxonomy of Conyza are discussed.