Cover crops (CCs) are able to affect subsequent crop behaviour by acting on many soil variables and affecting the dynamics of different ecological processes. This study aimed to investigate the effects of introducing CC in continuous-maize cropping systems within Mediterranean areas. The experimental site was located in Central Italy, on a sandy loam and the research activity was carried out over two years (2019–2020). The two cropping systems in comparison differed from each other in terms of the CC cultivation: TR (treated, with CC) and CO (control, without CC). In both years, we observed a significant reduction (p < 0.05) of soil nitrate and water content for the TR system. In the shallowest layer (0–30 cm), nitrate content was reduced by up −80% and −65% (July 2019 and 2020), whereas soil moisture showed decreases ranging from −13% (July 2019) to −34% (May 2019). In 2019, the TR-maize (Zea mays L.) yield was statistically lower than CO (−443 g dm m−2), whereas in 2020 the yields of the two systems resulted statistically equivalent. This different behaviour can be explained with the serious delay in the CC sowing occurred in 2019 (12 December). Conversely, an increase in the apparent remaining N in the soil (+140 and +133 kg N ha−1 for 2019 and 2020, respectively) and in the C (carbon) inputs (+4.78 and +7.39 t dm ha−1 of biomass) were pointed out for the TR system. The large use of inputs in Mediterranean maize cropping systems limited some of the benefits from CCs, but their suitability has to be evaluated by considering all the involved effects, some of which need a long time to become appreciable.