The emergence of vascular plants, such as Cooksonia, had a profound impact on Earth’s Early Paleozoic biogeochemical cycles (e.g. atmospheric oxygen, nitrogen and CO2), potentially triggering global environmental and biological changes. However, the timing of Cooksonia’s terrestrial emergence remains elusive as phylogenetic models, microfossils and macrofossils provide different timings for land colonization by vascular plants. Here, hundreds of zircon grains from three siltstones were dated using Laser Ablation-Inductively Couple Plasma-Mass Spectrometry (LA-ICP-MS). The study presents detrital zircon U-Pb dates, which refine the current biostratigraphy ages assigned to Cooksonia macrofossils from the three oldest sites globally. Specifically, siltstones hosting Cooksonia macrofossils from Borrisnoe Mountain (Ireland) and Capel Horeb (Wales) yield Gorstian–Homerian maximum depositional ages (MDAs) of 426 ± 2 Ma and 427 ± 2 Ma, respectively. Additionally, Cwm Graig Ddu (Wales) yields a (Pridoli-Ludlow) maximum age of 423 ± 3 Ma. The findings provide the first detrital zircon U-Pb dates for the oldest Cooksonia macrofossils globally and contribute crucial maximum ages. These maximum ages are instrumental in refining future calibrations of molecular clocks and improving phylogenetic models, thus contributing significantly to a better understanding of Cooksonia’s evolutionary history, including its environmental and ecological impacts.