Assessing the impact of past and future urban land expansion on ecosystem services (ESs) is essential for the sustainable management of urban landscapes. Despite recent progress, it remains challenging to determine the influence mechanism of different urbanization stages and areas on ESs and their trade-offs/synergies. Here, we analyzed the responses of four ESs and their trade-offs/synergies to the spatial and temporal differentiation of urbanization in the Su-Xi-Chang region of China from 1990 to 2050. The results showed that the relationship between ESs and urbanization followed a U-shaped curve from 1990 to 2050. Between 1990 and 2020, urbanization weakened trade-offs and enhanced lose-lose situations, exhibiting an S-shaped curve. From 2020 to 2050, lose-lose situations are expected to diminish, and the curve is projected to display a downward trend. Our findings suggest the implementation of compact urban development, sustainable agricultural practices, reforestation, and the conversion of farmland to lakes.