Improvement of household food security in the Limpopo Basin has been elusive due to a combination of factors related to information and market constraints, but also farmers’ risk aversion induced by the high variability of rainfall during the growing season. The purpose of this study was to (1) characterize the rainfall and growing season patterns experienced by smallholder farmers, and (2) measure soil water dynamics in ripper and basin tillage systems being promoted in the semi-arid Limpopo Basin of southern Africa. The results show that the second half of the growing season receives more rainfall than the first half in the Limpopo Basin. However, rainfall is more variable during the January-March than the October-December period. Growing seasons start earlier and end later in the Mozambique part of the basin which is closer to the Indian Ocean. The Limpopo Basin is prone to two and three week dry spells with chances of 14 day spells higher (34–42%) than the 21 day spells (8–12%). The chances of 14 and 21 day dry spells increase substantially during the second half of the growing season. The 1980–1990 was one of the driest decades in the Limpopo Basin. Planting basin system conserved more soil water on sandy loam (18–24%) and clay loam (4–12%) soils than the conventional practice during flowering and grain filling maize growth stages. Ripper had 17–29% more soil water than conventional practice during flowering and grain filling maize growth stages. There is a high risk of dry spells and soil water deficits in smallholder cropping systems of the Limpopo basin. There is therefore scope in promoting rain and soil water management technologies, and good land husbandry in order to reduce risk of crop failure in the smallholder cropping systems.