Risk is a major issue that affects so many aspects of people’s livelihoods in the developing world. It is imminent in all management decisions of agricultural systems, as a result of fluctuations in price, yield and resource uncertainty. Hence, uncertainty, risk aversion and management strategies were investigated among the cocoa farmers in Osun State, Nigeria. Primary data employed in the study were obtained from 102 cocoa farmers selected through a multi-stage sampling technique. Data were analyzed using descriptive statistics and multivariate probit model. Results showed that farmers view rainfall as the most important source of risk and uncertainty and majority of the farmers utilized mixed cropping as a risk management strategy in their farms. The result of multivariate probit model indicated that age of farmer negatively influenced the probability of precautionary savings while household number and access to information determined their choice of social network as risk management decisions used in the farms. The study recommends government policies and institutional mechanisms that reduce risk (such as crop insurance) and those that facilitate farmers’ access to assets like off-farm investments in order to manage risks.