Sensing fabrics have received great attention due to various applications in medical area, healthcare, and smart clothes. However, there are very few studies on sensing fabrics that can be used to monitor the pressure of compression garments. In this study, a pressure exerting and sensing fabric is fabricated by interweaving highly sensitive yarn sensor into woven fabric using industrial-scale weaving technology. By using a new method for measuring the pressure sensing capabilities under external stresses from a curved surface, effects of fabric structure and operation mode on the pressure and electromechanical properties are evaluated. New fabric structures are proposed to deliberately arrange the yarn sensing elements in a less-or even non-binding form within the fabric for good elasticity and sensing properties. Arising from the appropriate material selection and structure feature, the sensing fabric realizes a suitable and stable amount of induced pressure as well as very low stress relaxation. Consequently, the sensing fabric with sateen structure demonstrates very good pressure sensing performance with sensitivity of 1.22 kPa −1 , low hysteresis error of 8.06%, and linearity of 0.98 in the desired pressure range from 0.58 to 3.83 kPa. Furthermore, the fabric exhibits excellent stability over 4500 pressing cycles.