Leaf-beet is a typical and very important protected cultivation crop in central Italy. In leaf-beet protected cultivation, weed control is one of the most important problems because of its fairly long crop cycle (approximately 4–5 months). The aim of this research was to set up an efficient non chemical weed control strategy performed with innovative machines built and set up by the University of Pisa. A two-year (2006–2007) ‘on-farm’ experimental trial was carried out in Crespina (PI). A conventional weed management technique (consisting of one pre-transplanting chemical treatment) was compared with an innovative physical weed control strategy in an organic production system (consisting of using a stale seedbed technique, in several post-emergence precision hoeing and in-row hand-weeding treatments). In the conventional technique, leaf-beet was manually transplanted, while it was sown with a precision pneumatic planter in the organic system. All innovative machines for physical weed control were adjusted and set up for the protected cultivation. Similar yields were recorded for the two systems in this two-year trial. Total labor time (for weed management and crop planting) was appreciably lower in the conventional system in the first year of the experiment (−67%), while in the second year, some improvement in the physical weed control techniques decreased labor needs with respect to the conventional technique (−40%). Weed dry biomass at harvest was significantly lower in the organic cropping system (on average −50%).