Robotic solutions and technological advances for turf management demonstrated excellent results in terms of quality, energy, and time consumption. Two battery-powered autonomous mowers (2 WD and 4 WD) with random patterns were evaluated according to different trampling levels (control, low, medium, high) on a typical warm season turfgrass at the DAFE, University of Pisa, Italy. Data on the percentage of area mowed, the distance traveled, the number of passages, and the number of intersections were collected through RTK devices and processed by a custom-built software (1.8.0.0). The main quality parameters of the turfgrass were also analyzed by visual and instrumental assessments. Soil penetration resistance was measured through a digital penetrometer. The efficiency significantly decreased as the trampling level increased (from 0.29 to 0.11). The over-trampled areas were mainly detected by the edges (on average for the medium level: 18 passages for the edges vs. 14 in the central area). The trampling activity caused a reduction in turf height (from about 2.2 cm to about 1.5 cm). The energy consumption was low and varied from 0.0047 to 0.048 kWh per cutting session. Results from this trial demonstrated suitable quality for a residential turf of the Mediterranean area (NDVI values from 0.5 to 0.6), despite the over-trampling activity. Soil penetration data were low due to the reduced weight of the machines, but slightly higher for the 4 WD model (at 5 cm of depth, about 802 kPa vs. 670 kPa).