Application of tool-based micromachining in soft polymer has been limited due to high adhesion and low elastic modulus of this material at room temperature. This study aims to evaluate the machinability of a typical viscoelastic soft polymer and understand the effect of material and process parameters on machining performances. In this study, a micro-milling process using cryogenic-assisted cooling is proposed and the importance of temperature control toward glass transition zone was particularly addressed. To identify insight of machinability in micro domain, this article also determines minimum uncut chip thickness (MUCT) and size effects by considering the variations of cutting force and surface integrity with the ratio of h/re (uncut chip thickness (h) to cutting edge radius (re)). The experimental results reveal that consideration of size effect during micromilling of soft viscoelastic polymer helps in reduction of machined surface roughness (Sa) value. Based on the cutting force pattern, it is evaluated that higher machining stability can be achieved during cryogenic machining by reduction of specific cutting force value. Moreover, temperature range around glass transition zone yields more promising experimental outcomes, outperforming other cooling zones.