Rice-rice system and rice fallows are no longer productive in Southeast Asia. Crop and varietal diversification of the rice based cropping systems may improve the productivity and profitability of the systems. Diversification is also a viable option to mitigate the risk of climate change. In Eastern India, farmers cultivate rice during rainy season (June-September) and land leftovers fallow after rice harvest in the post-rainy season (November-May) due to lack of sufficient rainfall or irrigation amenities. However, in lowland areas, sufficient residual soil moistures are available in rice fallow in the post-rainy season (November-March), which can be utilized for raising second crops in the region. Implementation of suitable crop/varietal diversification is thus very much vital to achieve this objective. To assess the yield performance of rice varieties under timely and late sown conditions and to evaluate the performance of dry season crops following them, three different duration rice cultivars were transplanted in July and August. In dry season several non-rice crops were sown in rice fallow to constitute a cropping system. The results revealed that tiller occurrence, biomass accumulation, dry matter remobilization, crop growth rate, and ultimately yield were significantly decreased under late transplanting. On an average, around 30% yield reduction obtained under late sowing may be due to low temperature stress and high rainfall at reproductive stages of the crop. Dry season crops following short duration rice cultivars performed better in terms of grain yield. In the dry season, toria was profitable when sown earlier and if sowing was delayed greengram was suitable. Highest system productivity and profitability under timely sown rice may be due to higher dry matter remobilization from source to sink. A significant correlation was observed between biomass production and grain yield. We infer that late transplanting decrease the tiller occurrence and assimilate remobilization efficiency, which may be responsible for the reduced grain yield.