The goal of this study was to develop management strategies favouring establishment and survival of holm oak (Quercus ilex L.) and downy oak (Quercus pubescens Willd.)—two species co-occurring in Southern France—in mature Allepo pine forests (Pinus halepensis Mill subsp. halepensis). An experimental design was assessed in a partially cut mature stand of Aleppo pine in which five soil and vegetation treatments—chopping, chopping followed by scarification in one or two directions, prescribed burning, control—and two slash treatments (presence/absence) were applied. A total of 1,600 sowing points, each composed of 3 Q. ilex or Q. pubescens acorns, were installed in the different treatments in November of two consecutive years at 6 and 18 months, after the end of treatments. Survival was monitored 3 and 2 years after sowing, soil surface at the sowing points was characterized at different dates, and predawn leaf water potentials were measured during the dry season. High mortality occurred after the first summer, but survival after 1 year was 2.3–5.2 higher in Q. ilex than in Q. pubescens, confirming that Q. ilex was better adapted to the drier parts of the Mediterranean area. Survival was significantly influenced by the treatments, but there was a variable response between the two sowing years under most of the treatments. Only intense fire proved the most beneficial treatment for seedling survival in both years. The micro-local soil cover conditions induced by the treatments played a major role in explaining oak survival. In particular, grass cover (mainly Brachypodium retusum) proved to be largely unfavourable to seedling survival and growth, and this detrimental effect was also confirmed by lower predawn leaf water potential values with increasing grass cover. Acorn introduction designed to diversify mature Aleppo pine forest after soil and vegetation treatments therefore has to be considered for treatments that most efficiently impair the pre-existing competing grass cover such as prescribed high-intensity fire treatment.