In sustainable agricultural systems, intercropping using living mulches (LM) provides many beneficial ecosystem services. The objective of these two-year field experiments was to study the suitability of different LM options of burr medic (Medicago polymorpha L. var. anglona) for organic cauliflower (Brassica oleracea L.) cultivation in two sites under Mediterranean conditions. In central Italy (Experiment 1) contemporary and delayed (to crop) sowings of LM were compared with a no-cover crop treatment, contrasting two local cauliflower cultivars and a F1 Hybrid. In southern Italy (Experiment 2) the sustainability of systems combining LM (anticipated and contemporary sowing compared with no-cover) and organic fertilisation strategies was assessed. The aboveground biomasses dry weights of cauliflower crop (heads and residues), burr medic and weeds were separately determined. Results suggested that in Experiment 1 the LM was not able to smother weeds establishment and growth, as a consequence of early sowing, while cauliflower yield was reduced. Moreover, the genotypes behaviour was greatly influenced by the LM sowing times. In Experiment 2, irrespective of the agronomic practices applied, climatic conditions notably influenced cauliflower cultivation and also reduced the mean yield. Therefore, the recorded differences between the two experimental sites highlighted the need to tailor the LM strategies to the different environmental conditions.