Despite long-time practice, the effect of cover crop (CC) cultivation on N supply and yield of subsequent sugar beet (SB) is not clear for the temperate climate of Central Europe. To elucidate, four field trials with oil radish, spring vetch, saia oat, and winter rye CCs were conducted on typical loessial soil in Germany. Mineral fertilizer N dose was varied as second factor: zero (N0) and optimum dose (Nopt). Biomass characteristics before winter, soil mineral nitrogen content in spring (SMN), and sugar yield and total plant N content of SB were measured. The CC N effect (Neff), calculated as the difference in SB N uptake after CC minus bare fallow, was computed for the periods sowing-summer (July/August) and summer-harvest. On average, sugar yield was decreased after rye and increased after vetch CC compared to bare fallow which was more pronounced under N0 than Nopt. In the period sowing-summer, characterized by a high SB N demand, Neff was close to 0 kg N ha–1 after rye and up to +30 kg N ha–1 after vetch. In contrast, Neff in summer-harvest was negative, amounting up to –80 kg N ha–1 after radish and rye. Regression analysis revealed a significant relationship between Neff in the period sowing-summer and the sugar yield difference between the cover crop treatments and bare fallow (R2 = 0.29). A multiple regression analysis (R2 = 0.68) indicated that high CC biomass combined with a large negative spring SMN difference between CC treatment and fallow caused a large yield penalty, which can be compensated for by elevated N fertilization. Moreover, CC management ensuring either a limited CC biomass or low SMN difference of CCs compared to fallow by e.g., later sowing, less vital CC species or early CC termination, will likely secure higher SB yield after CCs than fallow.