Cover crops are increasingly adopted in viticulture to enhance soil quality and balance the vegetative and reproductive growth of vines. Nevertheless, this sustainable practice has been only recently used for table grape viticulture, with results often contrasting. The aim of this study was to assess the effect of a fescue (Festucaarundinacea Schreb.) cover crop on soil quality, yield, and grape qualitative parameters in a table grape vineyard (cv “Italia”) located in southern Italy, comparing results with the conventional tillage. Soil organic carbon (C), total nitrogen (N), microbial biomass C (MBC), β-glucosidase (BGLU) and alkaline phosphomonoesterase (APME) activities were assessed during three growing seasons (2012–2014) and three phenological stages. The trend of soil chemical and microbiological properties was jointly influenced by the soil management system, growing season and phenological stage. Compared to conventional tillage, cover crops increased, on average, soil organic C, total N, MBC, BGLU and APME by 136%, 93%, 112%, 100% and 62%, respectively. Slight or no effects of cover crops were observed on grape quality and yield, except for 2012 (the driest season), when a yield reduction occurred. This study reveals that cover crops strongly enhance soil quality in the short-term, with potential advantages for grape production in the long-term.