Intercropping perennial legumes with trees can reduce Nitrogen (N) losses, due to the high amount of N accumulated in stable forms in the soil and permanent soil cover during the whole year. Although N cycling improvement in mature agroforestry systems (AFS) was well documented, there is a lack of knowledge regarding systems in transition to AF. In this work, we studied the association of two perennial forage crops, namely ryegrass (Lolium multiflorum Lam.) and sulla (Hedysarum coronarium L.), with 1-year old poplars, to evaluate: (i) the agronomic performance of sulla and ryegrass with vs. without intercropped poplar trees; (ii) the N-fixing ability of sulla in association with trees; (iii) the N transfer effect from sulla and growth promoting effect on poplar; and finally (iv) the nitrate leaching reduction due to the presence of poplar trees associated to forage crops. The layout was arranged in a two-factor randomized complete blocks design (RCB) with three replicates. The first factor tested (crop species) implied two different swards, namely sulla and ryegrass. The second factor (cropping system) included two different systems: PAST i.e., a pastoral system without trees, and SIPAST, i.e., a silvo-pastoral system with one poplar tree row beside the sward. Sulla resulted more productive than ryegrass when associated with trees (+35%). No clear trend was observed about the tree influence on N-fixation in sulla, but the amount of N fixed resulted higher in in sulla grown in the SIPAST near the trees (+35%). Poplar plants, even in the first year after planting, resulted effective yet in reducing the nitrate flux from the crops towards ditches. Further investigations are needed to study other swards in young AF and better understand the N dynamics; in particular, it could be worth to assess the nutrient flux in the soil solution.