New trends related to market incomes, cultural human development, non-sustainable soil management practices, and climate change are affecting land abandonment in Mediterranean sloping vineyards. It is generally accepted that hydrological processes and, subsequently, soil erosion rates are usually different between cultivated and abandoned soils. However, these alterations are still poorly studied in relation to the general weather conditions in vineyards and abandoned vineyards. Thus, the main goals of this research are to (1) estimate the differences in soil properties, (2) quantify water and soil losses due to rainfall and specific soil management practices, and (3) analyze which kind of weather type and rainfall event is able to generate specific surface flows and soil loss rates. To achieve these goals, we focused on the specific case of the sloping vineyards of the Montes de Málaga (South Spain). We used 4 paired-erosion plots with Gerlach troughs to quantify soil loss and surface flow and conducted an analysis of the weather conditions during each rainfall event. The weather types that generated the highest amount of rainfall in the studied area came from the western (32.6%) and southeast (28.2%) types. The low rainfall events came from the south type (5.9%) and at the 500 hPa level, whereas the rainiest ones came from the southwest (47.7%) and south (34.1%). It is confirmed that there is a bimodality in the rainfall patterns. The results of soil erosion showed that there is a mixed mechanism depending on the state of the soil (vegetation cover, compaction, and initial soil moisture), soil management (tillage, trampling effect, and the use of herbicides). It is observed that the intensity of surface flow is highly correlated to the total rainfall amount and intensity. In the poorly managed abandoned plot, it is important to remark that the effect of tillage in the past, the elimination of the vegetation cover to preserve the soil in bare condition, and its use as a grazing area by cultivating barley highly affects the generation of the highest erosive events. Therefore, it is confirmed that these soil management options are not the most sustainable way to conserve the soil after the abandonment of cultivation.