We present Sunyaev-Zel'dovich Effect (SZE) scaling relations for 38 massive galaxy clusters at redshifts 0.14 ⩽ z⩽ 0.89, observed with both the Chandra X-ray Observatory and the centimeter-wave SZE imaging system at the BIMA and OVRO interferometric arrays. An isothermal β-model with the central 100 kpc excluded from the X-ray data is used to model the intracluster medium and to measure global cluster properties. For each cluster, we measure the X-ray spectroscopic temperature, SZE gas mass, total mass, and integrated Compton y-parameters within r2500. Our measurements are in agreement with the expectations based on a simple self-similar model of cluster formation and evolution. We compare the cluster properties derived from our SZE observations with and without Chandra spatial and spectral information and find them to be in good agreement. We compare our results with cosmological numerical simulations and find that simulations that include radiative cooling, star formation, and feedback match well both the slope and normalization of our SZE scaling relations.