Central and Eastern Europe (CEE) is a pillar of global wheat and maize production. However, certain areas within the CEE region have become climate change hotspots, experiencing intensifying water deficits and drought pressure, rising mean and maximum temperatures. This study focuses on the long-term statistical relationships between climatic factors and rain-fed wheat and maize yields for different landscape types in Hungary over 30-year time windows between 1921 and 2010. The relationship between the variances of the detrended climatic parameters and crop yields was tested employing both simple and multifactorial linear models according to landscape types and periods. The sensitivity of wheat yields to spring–summer mean temperature shifted dynamically from the western part of the country to east (from cooler and wetter hilly landscapes to plains) between the periods 1921–1950 and 1981–2010. The cooling observed in summer temperature between the periods 1921–1950 and 1951–1980 supported an increase in wheat yields by an estimated 0.11–0.43 t ha−1 year−1, while the 0.9–1.2 °C warming of May–July temperature may have cut wheat yields by an estimated 0.44–0.56 t ha−1 year−1 in various regions over 1981–2010. That being said, the regional sensitivity of wheat yields to May–July mean temperature did not display substantial differences between the periods 1921–1950 and 1981–2010. Besides negative effects, climate change had a positive impact on wheat yields, since increasing January–March mean temperatures mitigated the negative impact of warming summer temperatures on wheat yields by an estimated 16–34% over 1981–2010. In this 30-year period, increasing mean temperature together with decreasing precipitation explained 46–75% of the variances in maize yields reducing annual maize harvests by an estimated 11.1–12.4% year−1.