Limitations to the current perennial ryegrass-based pasture system on dryland dairy farms in southern Australia has led to research into alternatives that can produce either additional DM, out of season feed or can improve nutritive characteristics. The use of winter annual crops followed by a summer crop have the potential to achieve these goals but often result in considerable periods where new crops are establishing and feed is not available for consumption. Companion cropping offers an option to overcome these limitations. The experiment reported in this paper examines the DM yields, nutritive characteristics and mineral content of companion cropping wheat or triticale at different sowing rates into an existing chicory monoculture over a 2-year period. We hypothesised that oversowing cereal crops in autumn into an existing stand of chicory would result in improvements in nutritive characteristics at ensiling, without adversely affecting DM yield or subsequent chicory DM yields following harvesting, thus negating the need to sow a new summer forage crop each year. Total DM yields for the chicory and cereal monocultures were similar over the experimental period, while DM yields for all triticale mixtures were higher than the chicory only treatment. Chicory produced lower DM yields for silage but higher DM yields at most grazing events. The crude protein and estimated metabolisable energy content of the chicory only treatment was higher than the cereal monocultures and all triticale/chicory mixtures at both silage harvests with wheat/chicory mixes being intermediate. The proportion of chicory in the mixed swards declined over the course of the experiment. The use of chicory with cereals resulted in no adverse effects on total DM yields, some improvements in nutritive characteristics and mineral content and a more continuous supply of DM compared with double cropping with annual species in winter and summer. This experiment has highlighted the potential of oversowing cereal forages into an existing chicory sward to contribute to DM production on dairy farms in southern Australia. Such forage mixes can provide flexibility into forage systems through the provision of forage for grazing in early winter, the production of high DM yield silage harvests and then subsequent feed supply over summer and early autumn.