Floral fertility of five primocane-fruiting (PF) blackberry (Rubus L. subgenus Rubus Watson) genotypes (‘Prime-Jim’®, APF-31, ‘Prime-Ark® 45’, APF-59, and APF-77) and three floricane-fruiting (FF) genotypes (‘Navaho’, ‘Natchez’, and ‘Ouachita’) were tested under field conditions using floricane flowers with four pollination treatments: undisturbed open-pollinated, emasculated self-pollinated, emasculated and cross-pollinated with pollen from a similar fruiting type (PF × PF or FF × FF), and emasculated and cross-pollinated with pollen from a different fruiting type (PF × FF or FF × PF). During primocane flowering, three pollination treatments (undisturbed open-pollinated, emasculated selfed, and emasculated cross-pollinated) were used to further test the fertility of the five PF genotypes. Significant differences between cross-pollination treatments and self-pollination were seldom noted with more differences seen in ‘Prime-Jim’® than any other genotype. Cross-pollinating primocane flowers on ‘Prime-Jim’® resulted in significantly higher fruit set, drupelet set, and average berry weight compared with self-pollination. Fruit set among genotypes ranged from 68.5 to 96.7%, and drupelet set rating ranged from 4.3 to 6.9 for floricane flowers. For open-pollinated primocane flowers, fruit set ranged from 63.9 to 92.1%, and drupelet set rating ranged from 4.3 to 7.2. The genotypes APF-31, APF-59, and APF-77 showed a marked improvement over ‘Prime-Jim’® in both percent fruit set and drupelet set of floricane and primocane flowers. The results indicated that fertility appears to be sufficient in all the genotypes evaluated and that the later-generation PF genotypes show improvement in fertility over ‘Prime-Jim’®. Pollen viability (using both chemical viability testing and in vitro germination testing), stigma receptivity, and pollen tube growth (using florescence) were evaluated in a controlled environment to determine if any improvements could be noticed when comparing a selection of later-generation PF genotypes (APF-31,' Prime-Ark® 45', APF-59, and APF-77) with ‘Prime-Jim’® and ‘Prime-Jan’®. Genotypes APF-31, APF-59, and APF-77 had significantly more viable pollen and pollen germination than ‘Prime-Jan’®. Stigma receptivity was observed in all genotypes. Pollen tube growth did not appear to be inhibited after self-pollination in any genotype studied, although significantly greater florescence resulting from pollen tube growth was seen after cross-pollination compared with self-pollination for APF-59. There were no significant differences in pollen tube growth between cross- and self-pollination for any other genotype.