With global warming, the cultivation area of bermudagrass is moving northwards in the Mediterranean area despite its winter dormancy and loss of green color. The most common solution is overseeding with perennial ryegrass, which can be complicated to remove in spring. DLF breeders have released a new cultivar of annual ryegrass that is stress tolerant and easy to transition in spring. A trial was carried out on a sod farm in Pisa, Italy. Twenty-nine varieties of cool-season grasses, encompassing both forage and turf species, were overseeded on a hybrid bermudagrass variety ‘Tifway’ (Cynodon dactylon x transvaalensis). The aim of this trial was to compare the overseeding potential of various cool-season turfgrass species and cultivars and to identify which ones perform best in terms of cleanness of cut when overseeded on hybrid bermudagrass in autumn and maintained at a mowing height of 25 mm. Moreover, the following parameters were also assessed: actual turf height (cm); cumulated height (cm); turf visual color and quality (1–9 scale); and visual ground cover (%). Plots were managed with an autonomous mower, which adopted a daily mowing frequency and was set to work with systematic trajectories. The results showed differences between cultivars, and the annual ryegrass showed the best spring transition (scoring a mean value of 96% green cover in July 2023) compared to the other entries. The best result of CoC was measured for rough-stalked meadow grass ‘Sabrena 1’ and tall fescue ‘Turfway’ with 0.9 mm.