Compression therapy using bandages or socks is the most common treatment for venous leg ulcers and edema. This article aims to compare the compression between long- and short-stretch bandages (LSB and SSB, respectively). Load-elongation curves, cyclic loading, and elastic recovery are investigated for both Cotton/Polyamide/Polyurethane and 100% bleached cotton bandages as LSB and SSB, respectively. Static (resting) and dynamic (working) pressures are measured on seven male legs, 31 ± 3.6 years old, using both two and three layers bandaging. Picopress pressure tests are performed on the ankle and mid-calf positions at gradual decreasing compression from the ankle to the knee. The deviation percentage between the experimental results by Picopress and theoretical calculations using Laplace's law and Al-Khaburi equations is compared. LSB recovered approximately 99% of its original length after stress-relaxation whereas SSB recovered only 93% of its original length after 5 days of cyclic load-relaxation. Moreover, SSB lost approximately 28.6% of its activity after wearing on the human leg for 5 days.