The need to redesign more sustainable agricultural systems able of producing more, especially through intercropping or agroforestry, cannot be achieved without taking into account the essential aspect of production variability. Yet, although many studies have focused on the effect of intercropping on overall production, the particular issue of production variability in such systems remains relatively unstudied. The approach we propose, for a shift towards sustainable intensification of agricultural systems, considers the dual dimensions of yield and risk in a combined framework for the assessment and the comparison of two diversification strategies: (i) a simple diversification strategy (SDS) considered as an increasing number of crops grown on separate plots within a farm and (ii) an intercropping strategy (IC) considered as a within-plot increased diversity, where more than one species is grown at the same time and place. The two perspectives examined here were Modern Portfolio Theory and Land Equivalent Ratio. The former quantifies the effect of diversification on risk, the latter measures the effect of association on production. This research merges both approaches in a combined framework in order to assess intercropping system performances. By applying our framework to cases selected from the literature, we explored and compared the potential benefits of these two strategies in terms of yield and risk. Results showed that intercropping, in addition to being interesting with regard to yield, can have an additional risk reduction effect compared to a simple diversification strategy. Conversely, some crop mixtures maintained or even increased yield variability. Our work contributes to a better understanding of the possible impacts of diversification strategies on trade-offs between yield and risk, but also underlines the importance of taking yield variability into account in further studies.