The effects of earthworm inoculation and cropping systems on upland rice systems were examined over a four-year period in the Highlands of Madagascar. Each year, endogeic earthworms Pontoscolex corethrurus (Rhinodrilidae) were inoculated (EW+) at a density of 75 ind m−2 or were not inoculated (EW0). Inoculation was tested in three cropping systems: conservation agriculture (CA) and traditional tillage with or without residues restitution. Soil and plant properties were measured during the first three years while soil biological properties were assessed at the fourth year. At the end of the experiment, earthworm density was three-fold higher in EW+ than in EW0, demonstrating the success of the inoculation. Earthworm density was more important in CA than in tillage systems. Earthworm inoculation had higher significant effects on soil and plant properties than cropping systems. Earthworm inoculation had positive effects on soil macroaggregation (+43%), aboveground biomass (+27%), rice grain yield (+45%), and N grain amount (+43%). Intensifying earthworm activity in field conditions to meet the challenge of ecological transition is supported by our study.