Sweet cherry (Prunus avium L.) cultivation is rapidly expanding in Northern Italy, where excessive vegetative vigor often limits fruit set and quality. This study aimed to evaluate the effects of Prohexadione-calcium (Pro-Ca) on the vegetative growth, productivity, and fruit quality of cv. ‘Tip Top’ sweet cherries grafted onto Gisela 6 and MaxMa 14 rootstocks. The growth regulator was applied twice between the flower bud and petal fall stages. Pro-Ca significantly reduced vigor and increased the fruit setting by 10%, resulting in an yield average of +3 kg per plant. Also preharvest treatment increased average cherry size compared with the control, particularly in plants grafted onto Gisela 6. Moreover, Pro-Ca-treated fruits exhibited a +20% red overcolor extension of the skin, improved skin firmness (+12%), and led to higher nutraceutical properties. In conclusion, Pro-Ca improved plant yield and fruit quality in ‘Tip Top’ sweet cherry, likely through the combined effects on hormonal balance, assimilate allocation, and canopy light distribution, supporting its potential as a valuable growth regulator in high-density sweet cherry orchards.