Woody plants, foundational to terrestrial ecosystems, have evolved sophisticated molecular mechanisms to cope with recurrent drought stress. Post-translational modifications are critical for rapid, dynamic cellular responses, with ubiquitination and SUMOylation serving as key pathways that modulate protein properties to fine-tune drought signaling and adaptation. This review synthesizes recent advances in the ubiquitin and SUMO systems in woody plants under drought. We outline the core components of these two post-translational modification pathways, detail how ubiquitination regulates key transcription factors and abscisic acid (ABA) signaling, and explore the multi-level effects of SUMOylation, from substrate modification to chromatin remodeling, as well as the crosstalk between ubiquitin and SUMO. Furthermore, we specifically discuss and emphasize the distinctive functional roles of ubiquitination and SUMOylation, their evolutionary basis in the context of woody plants' long lifespans and complex developmental processes, and their contributions to adaptation and acclimation mechanisms. By integrating genetic, genomic, and proteomic evidence, this review provides theoretical insights and molecular targets for improving drought resistance in forest trees, thereby supporting research on sustainable forestry and climate change resilience.