Pruning residues from olive groves represent an important biomass source. Until now, the management of pruning residue has generally represented a disposal problem rather than an opportunity for additional revenue. The main problem is the lack of a well-organized pruning biomass supply chain. In particular, harvesting is a key stage that influences the product quality, the type of logistics chain, and the economic sustainability of the pruning supply chain. The aim of the present paper was the evaluation of the machine performance of the Facma Comby TR200 towed shredder. The harvesting tests took place in Agios Konstantinos, Fthiotida, Central Greece. Two different experimental fields were used for the evaluation of this harvesting system; these fields were characterized by different slopes to check the convenience of using such a towed shredder on both hilly slopes and flat terrains. Analysis was conducted focusing on both the work productivity and costs. Moreover, an evaluation of the obtained hog fuel quality was performed. The Facma Comby TR200 showed good work performances on both flat (2.60 tdm·h−1) and hilly (2.74 tdm·h−1) land, even if a consistent influence of the pruning biomass yield on the work performances was reported. The biomass quality could be consistently improved by modifying the pick-up systems to avoid the collection of inert materials (soil and rocks). In fact, the analysis showed a high ash content in the comminuted material (4% dry basis). Finally, the economic aspects of this study’s results were in line with those reported in the literature. The applied harvesting system showed a cost equal to 29.88 and 16.59 €·tfm−1 on flat and hilly land, respectively.