Cucumber plant growth and the fate of N in the plant-soil system are influenced by fertilization practices, the strengths of which may vary among soils. Three soils with different years of greenhouse vegetable cultivation (0, 2, and 18 years) were fertilized differently (CK, no N fertilizer applied; CF, chemical NPK fertilizers applied; RCF, reduced chemical NPK fertilizers applied, with N, P, and K reduced by 46.5%, 68.6%, and 54.7%; RCF+CM, 75% of the total N derived from chemical fertilizer and the rest from chicken manure in the case of reduced fertilization) in a pot experiment to study the changes in cucumber (Cucumis sativus L.) growth, N uptake, residue, and losses. The original N in soil was insufficient to maintain leaf growth and chlorophyll synthesis at later growth stages, even in soil with 18 years of greenhouse vegetable cultivation, where the original N content was the highest (total N 1.73 g kg−1). However, the CF treatment with excessive N fertilization inhibited leaf growth at the early growing stage and accelerated leaf senescence later, especially in soil with longer years of greenhouse vegetable cultivation. Therefore, reduced fertilizer application (RCF and RCF+CM) is appropriate to improve cucumber growth and productivity in greenhouse cultivation with different planting years. Although the same amount of N was applied, the RCF+CM treatment performed better than the RCF treatment in terms of increasing plant N uptake (by 30.5%) and soil N pool storage (by 25.0%) while decreasing N losses (by 16.6%) in soil with 0 years of greenhouse vegetable cultivation. In soil with 2 and 18 years of greenhouse vegetable cultivation, the soil itself functions much better in exogenous N retention and supply, with the N storage and losses not significantly different between the RCF and RCF+CM treatments. We conclude that reduced fertilization with the co-application of chicken manure is optimal for plant growth promotion, output-input ratio increase, soil N fertility improvement, and environmental risk mitigation.