The ecosystem services a cover crop (CC) provides depend enormously on species choice and tillage system. Here, we evaluated the impact of (a) three winter CCs—rye (Secale cereale L.) and squarrose clover (Trifolium squarrosum L.) monocultures and their mixture, and (b) two tillage systems—roller-crimping of CC residue as dead mulch for no-till (NT) systems and incorporating CC residue into the soil as green manure for conventional tillage (CT) systems—on the performance of organic processing tomato, i.e., plant growth, nutrient accumulation, fruit yield, and weed biomass. The assessments took place over two years in field experiments conducted under Mediterranean conditions. At the termination time, rye and mixture were the most productive and the best weed-suppressive CCs. During tomato growing season, squarrose clover regardless of tillage system stimulated tomato growth, Nitrogen content and uptake, and the yield relative to the other cover crops. Nevertheless, NT generally impaired the tomato nutritional status and increased weed biomass compared to CT despite some potential weed control by cover crops. These two aspects caused a significant drop in tomato yield in all NT systems. The results suggested that, despite the multiple benefits the compared CCs can offer in Mediterranean agroecosystems, legume CCs could be the key to developing feasible organic vegetable no-till systems.