Weed management is not yet environmentally, agronomically, economically and socially sustainable in olive orchards. It is necessary to study appropriate integrated weed management systems (IWMSs) based on the knowledge of weed population and effects of weeding practices over time. The aim of this study was to evaluate the effects of different weed managements on seasonal floristic composition of a super high-density olive orchard, also exploiting the essential principles of an IWMS. Five weeding techniques were compared: chemical control (CHI), mowing (MEC), plastic (nonwoven tissue, TNT and polyethylene, PEN) and organic (with de-oiled olive pomace, DOP) mulching. Weed monitoring was carried out on six dates in a three-year period. The infestation of each of the main 18 weed species recorded (%) and the total infestation (%) on each monitoring date were determined. Results underlined that all weeding practices investigated in this multi-year study affected the floristic composition, weed characteristics (hemicryptophytes, cryptophytes and therophytes) and seed bank. TNT and PEN were the most effective methods for weed management. Particularly, total infestation coefficient was significantly lowest when plots were managed with TNT (13.91%) and PEN (14.38%) and highest for MEC (141.29%). However, DOP also significantly reduced infestation compared to CHI and MEC. Therefore, DOP could constitute an excellent strategy for weed management in super high-density olive groves, since it also has the possibility of distributing mulching materials in a mechanized way in field and can result in improvement of soil fertility and the possibility of valorizing waste. Further studies should be carried out to investigate the mechanism of action (physical and allelochemical) of de-oiled pomace or other organic agro-industrial materials and the recovery time of these mulching materials in super high-density olive orchards.