It is essential to achieve the optimum stretch for the 100% cotton woven compression bandage (WCB), particularly when producing short-stretch bandage (SSB). Since the SSB achieves a high level of working pressure (dynamic or walking) and a low level of resting pressure (supine or sleeping), this study evaluated the effect of ply twist on yarns extension that are being used as warp yarns in WCB. The proposed study investigated the commercial yarns available in the bandage market in addition to yarns spun at a wider range of ply twist. Moreover, the study analysed the influence of yarn material and bandaging technique on corresponding pressure at the ankle and mid-calf positions. Results revealed that the optimum twist for plied yarn should be at least 1800 turns per meter to produce highly extensible WCB. The experimental results of the uniaxial stress test concluded that the elasticity of 100% cotton short-stretch bandage followed the exponential behaviour whereas the cotton-polyamide-polyurethane long-stretch bandage behaved in a linear function due to the higher level of elastic recovery gained by polyurethane (Elastane) filament.