Relay intercropping is considered a valuable agroecological practice to increase and stabilize crop yields while ensuring the provision of several ecosystem services as well as sustainability and resilience to changing climatic conditions. However, farmers are still reluctant in the use of intercropping practices since there is a huge knowledge gap regarding the time of sowing, sowing ratio, crop stand density, and cultivar choice. In this study, we carried out a 3-year field experiment in Central Italy to assess the effect of relay intercropping on the agronomic performance and competitiveness of winter durum wheat (Triticum durum Desf. cv. Minosse) and spring lentil (Lens culinaris Medik. cv. Elsa) under a low-input management system, comparing different crop stand types (monocrop vs. intercrop) and target plant densities (350 plants m2—full dose vs. 116 plants m2—1/3 dose). The results revealed that intercropping increased grain yield compared to monocropping: significantly (p < 0.0001) against both monocrops in 2021 and non-significantly against durum wheat in 2019 and 2020. Yield advantage in both intercropping systems ranged between 164 and 648%. Durum wheat competitiveness was stronger in 2019 and 2021, while lentil was the most competitive component in 2020. Intercropping favored P accumulation in durum wheat shoots. There was no difference in grain yield of both crops between the highly- and lowly-dense system in 2020 and 2021. Both intercropping strategies were as effective as mechanical hoeing in controlling weeds and proved beneficial in stabilizing lentil productivity. Further economic analysis capturing the additional costs incurred in intercropping and mechanical weeding would highlight the magnitude of profitability of these systems.