In this work, we prepared poly(caprolactone) (PCL) monofilaments incorporating different amounts of the antiseptic chlorhexidine diacetate (CHX) and evaluated the effect of "online" drawing during the melt spinning or of an "offline" cold drawing on the antimicrobial and physical properties of PCL/CHX monofilaments. The results showed that the drawing conditions strongly affected the properties of the threads. In particular, the filaments exhibited antimicrobial activity for all the draw ratios (DR) adopted, but on increasing DR the antibacterial efficiency reduced. These results were correlated with the CHX surface concentration and with the release kinetics.