Traditionally, due to its light ecology, oak is regenerated on clear cuts or areas where the crown coverage is heavily reduced. Thus, the regeneration phase is relatively short. Recently, selective long-term regeneration phases avoiding large gaps in the canopy but fostering mixed-species stands have been advocated as being more in keeping with close-to-nature forestry in Central European forests. However, examples of the successful regeneration of oak in mixtures following this type of regeneration are largely missing. Here, we report the results of long-term experiments located in three different forest types, where oak was long-term regenerated under different mixing and canopy cover situations. The observation periods reached from 26 to 36 years. We focused on the dynamics of stem number reduction, as well as the height and biomass development of oaks and their interaction with interspecific competition and canopy density. The probability of oaks occurring in the regeneration basically decreased over the duration of the regeneration period. Despite this, considerable regeneration biomass growth could be observed, especially in the case of the lower standing volume of the mature stand. The development of beech as the main competitor is scarcely slowed down by the canopy cover compared to oak. Increasing canopy cover noticeably impeded oak regeneration in the considered mixed stands. The model results suggest that a reduction in competition within the regeneration by lowering the proportion of beech below 30% enhanced the success of oak regeneration in the long run even in small patches. The productivity of the remaining stand was primarily driven by standing volume. However, a negative trend of its productivity emerged with high regeneration biomasses. The study results show that small-scale oak regeneration with prolonged regeneration duration is possible in principle. However, oak regeneration requires active and continuous silvicultural assistance, which has to be adjusted to the specific site conditions.