Short-rotation coppice (SRC) represents an important source of wood biomass. Many uncertainties create barriers to farmers establishing SRC plantations, especially under Mediterranean climate conditions. In this study, five species and respective genotypes were analyzed. The five species were Fraxinus angustifolia, Robinia pseudoacacia, Salix alba, Populus nigra (Limatola), and Populus × euroamericana, with the genotypes of the latter being Grimminge, Vesten, Hoogvorst, Muur. For the plantations studied, two different harvesting systems were replicated: the single machine pass, or cut-and-chip (CC); and the double machine pass, for which the tree are cut first, then chipped later (chip of stored trees CS). In the CC, fresh trees were harvested and chipped by Claas Jaguar 880. In the CS, dry trees were chipped by Farmi Forest CH 260. Within the same site, in climatic conditions and low-input management, the best result in terms of biomass yield was obtained from the black poplar Limatola. Both wood typologies and harvesting systems affected the chip quality. The disk chipper, when working on dried biomass, produced lower quality chips than the other chipping device in terms of particle size. In the chips obtained, there was an increase in the number of chips classified as being “larger size” and “oversized”, and a decrease in the percentage of those classified as “accept” (45–3 mm fraction). The chips obtained from dried trees were of better energy quality compared with the same biomass obtained from the fresh trees in terms of heating value and ash content.