Cover crops are multifunctional, and contribute to improving soil properties and reducing environmental impact compared to no-cover crops, thus could provide multiple soil, agricultural, and environmental benefits, and they are recognized as a valid strategy for the achievement of sustainable agriculture. However, cover crops’ impacts on subsequent cash crops and soil characteristics are dependent on several factors, such as pedoclimatic conditions, cover crop species, agricultural practices, method of termination, and irrigation management. The fact that cover crops are never applied as a single practice in the real agricultural sector, but are instead combined with other factors or agricultural practices, deeply affects their performance, but the scientific literature nevertheless keeps considering the use of cover crops alone. Moreover, the potential outcomes of cover crops that encompass other factors or agricultural practices affecting soil quality, weed control, and cash crops are still unclear. Additionally, cover crops are still poorly use in the Mediterranean type of climate. Therefore, this study reviewed the scientific literature to identify the most relevant factors or agricultural practices driving cover crops’ performance, and to outline future fields of investigation looking towards promising sustainable agriculture in Mediterranean areas with a view to minimizing the competition for soil water with the cropping systems and to reduce soil degradation. Furthermore, the investigation includes multiple factors or agricultural practices that better represent the real farming system, contributing to a comprehensive understanding of their interactions with cover crops, and suggests alternative strategies for reducing yield gap while seeking to achieve agricultural sustainability.