Under continuous no-till, gypsum has been successfully used to manage soil fertility and improve crop yield. Nitrogen (N) fertilization is critical for crop performance, however, since it is expensive and potentially pollutant, it must be correctly applied. Both subjects have been widely studied, yet there is a lack of information on the interaction between them, especially concerning crops in rotation or succession. The objectives of this study were to evaluate topdressing N fertilization (0, 50, and 100 kg N ha −1 ) on black oat (Avena strigosa Schreb.) under no-till, inside a long-term gypsum experiment (0, 3, 6, 9, and 12 Mg ha −1 ). We evaluated black oat regrowth after haylage harvest and nutrient concentration and uptake by aboveground biomass, as well as the effects of this system on the successor crop soybean (Glycine max (L.) Merr.) in terms of leaf nutrient concentration and grain yield over two growing seasons. The gypsum application, even up to 44 and 55 months earlier, presented a long-term effect when associated with N fertilization, causing black oat biomass to increase during the regrowth phase. Nitrogen fertilization increased black oat regrowth biomass, even without gypsum. Greater nutrient uptake by black oat regrowth occurred under higher gypsum rates and N fertilization, which may have been advantageous in the long term for the production system, once nutrient cycling may partially substitute fertilizer-derived nutrients. Soybean yield was not affected by either long-term gypsum or N applied at black oat tillering, even though some leaf nutrient concentrations were influenced.