Ripe rot of grape is caused by two fungal species complexes: Colletotrichum gloeosporioides and C. acutatum, both of which cause disease on a variety of crops, such as strawberry and apple. To investigate effect of cultivar and cluster developmental stage on the development of ripe rot, controlled environment and field studies were conducted during 2013-2014. We have identified that a certain level of infection could can take place on most cultivars tested from bloom to the near harvest. In most of the cases, significant cultivar and cluster developmental stage interaction effects were observed (P < 0.05) for the development of disease symptoms in both studies. In general, susceptible cultivar (Cabernet Franc, Cabernet sauvignon, and Chardonnay) demonstrated fluctuations of disease susceptibility among cluster development stages, while resistant cultivars (Merlot) showed consistently low level of the disease throughout the season. To investigate the effect of eleven ten modes of action for control of C. gloeosporioides and C. acutatum, two methods, alamarBlue® assay and inoculation on fungicide-treated detached fruits, were used. Protective fungicides (mancozeb, captan, and copper) as well as some of newer formulations such as azoxystrobin and tetraconazole were identified as excellent products against ripe rot of grape. Four additional materials were identified as good potential candidates to investigate further. The information gained from these studies will help growers to determine the critical period for ripe rot management and chemicals to be applied for management. With better control of cluster rot pathogens, Virginia growers can experience an increase in yield and wine quality.