Drought is a serious constraint to crop growth and production of important staple crops such as winter wheat and maize. Improved understanding of crops' response to drought can be incorporated into cropping system models to support crop breeding, crop and varietal selection and management decisions to minimize negative impacts. Plants may respond to drought through immediate stomatal regulation as well as possibly altering their morphological characteristics over longer periods. The degree and combination of these short- and long-term responses depends on the intensity and duration of drought as well as crop characteristics. However, field observational evidence for different crop types detailing these at short- and longer term responses and for different organizational levels is still limited. Here we examine the effects of various water supply treatments on short-term changes in leaf water potential (LWP) and gas exchange at the leaf level together with the seasonal changes in canopy photosynthesis, transpiration, and cumulative growth of winter wheat and maize based on field data collected in 2016, 2017, and 2018. Leaf and canopy gas exchange and cumulative growth was varied strongly with the duration and intensity of drought stress as well as growing stages. The longer-term morphological drought responses in winter wheat appeared to have a larger effect on regulating transpiration and assimilation rates than shorter-term responses of stomatal control had. Maize (grown in 2017 and 2018) exhibited different responses, with seasonal variations in minimum LWP and complete stomatal closure at LWP of between -1.6 and -2 MPa. While stomata closed with increasing drought, for maize, the physiological advantages of C4 photosynthesis as well as morphological adjustments in leaf area size and leaf-rolling strongly determined crop growth and canopy gas exchange in the drought plots as compared with the irrigated plot. Observations highlight that improvements for soil-vegetation-atmosphere models in simulating gas exchange and crop growth should emphasize the dynamic reduction of leaf area under water stress, as well as stomatal regulation.