Nanocrystalline diamond (NCD) membranes are promising candidates for use as sensitive pressure sensors. NCD membranes are able to withstand harsh conditions and are easily fabricated on glass. In this study the sensitivity of heavily boron doped NCD (B:NCD) pressure sensors is evaluated with respect to different types of supporting glass substrates, doping levels and membrane sizes. Higher pressure sensing sensitivities are obtained for membranes on Corning Eagle 2000 glass, which have a better match in thermal expansion coefficient with diamond compared to those on Schott AF45 glass. In addition, it is shown that larger and more heavily doped membranes are more sensitive. After fabrication of the membranes, the stress in the B:NCD films is released by the emergence of wrinkles. A better match between the thermal expansion coefficient of the NCD layer and the underlying substrate results in less stress and a smaller amount of wrinkles as confirmed by Raman spectroscopy and 3D surface imaging. ; This work was financially supported by the Hasselt University Special Research Fund (BOF). The Hercules Foundation Flanders is acknowledged for financial support of the Raman equipment. SDJ and PP are Postdoctoral Fellows of respectively the Japan Society for the Promotion of Science (JSPS) and the Research Foundation - Flanders (FWO).