Supplemental light (SL) is a technique used to increase horticulture yield, especially in northern countries, where the Daily Light Integral (DLI) is a limiting factor during fall and winter, and which could also be used to obtain higher tomato yield at the Mediterranean latitude. In this study, three tomato hybrid (F1) cultivars were grown for year-round production in a commercial semi-closed glasshouse in Southern Italy: two of the cherry fruit-type (‘Juanita’ and ‘Sorentyno’) and one mini plum fruit-type (‘Solarino’). From 120 to 243 days after transplant, light-emitting diode (LED) toplights were used as SL, with a photoperiod of 18 h. The main climatic parameters inside and outside the glasshouse were recorded, and tomato plants’ development and yield were examined. Plants grown with LEDs had longer stems as compared to control treatment (9.53 vs. 8.79 m), a higher stem thickness and yielded more trusses. On average, the yield was 21.7% higher with LEDs. ‘Sorentyno’ was the cultivar with the highest cumulated productivity when it was grown under SL. However, the cultivar with best light use efficiency under LEDs was ‘Solarino’. Therefore, supplemental LED from mid-December until March enhanced tomato growth and yield, opening a favorable scenario for large-scale application of this technology also in the Mediterranean area.