Conferring antimicrobial properties to a filament can be achieved during the spinning of the fibers by incorporating in the melt an appropriate biocide. However, it is important to highlight that in a typical melt spinning process, the polymer melt is pulled and cooled to form a solid filament and then, it is usually subjected to post spinning operations such as drawing. Consequently, it is crucial to understand as the spinning conditions affects the properties of the filaments. In this work we prepared polypropylene (PP) fibers incorporating an antibiotic, i.e. ciprofloxacin (CFX), by melt spinning. In particular, PP has been compounded with CFX at different concentrations by using a counter-rotating twin screw compounder. The PP/CFX fibers have been spun by using a capillary rheometer operating under a constant extrusion speed. The effect of “online” hot drawing during the melt spinning or of an “offline” cold drawing on the properties of PP/CFX fibers were evaluated. In particular, the influence of the drawing conditions on the mechanical properties and the release kinetics were studied. Moreover, the rheological behavior in non-isothermal elongation flow has been assessed.