Context Functional connectivity is vital for plant species dispersal, but little is known about how habitat loss and the presence of green infrastructure interact to affect both functional and structural connectivity, and the impacts of each on species groups. Objectives We investigate how changes in the spatial configuration of species-rich grasslands and related green infrastructure such as road verges, hedgerows and forest borders in three European countries have influenced landscape connectivity, and the effects on grassland plant biodiversity. Methods We mapped past and present land use for 36 landscapes in Belgium, Germany and Sweden, to estimate connectivity based on simple habitat spatial configuration (structural connectivity) and accounting for effective dispersal and establishment (functional connectivity) around focal grasslands. We used the resulting measures of landscape change to interpret patterns in plant communities. Results Increased presence of landscape connecting elements could not compensate for large scale losses of grassland area resulting in substantial declines in structural and functional connectivity. Generalist species were negatively affected by connectivity, and responded most strongly to structural connectivity, while functional connectivity determined the occurrence of grassland specialists in focal grasslands. Restored patches had more generalist species, and a lower density of grassland specialist species than ancient patches. Conclusions Protecting both species rich grasslands and dispersal pathways within landscapes is essential for maintaining grassland biodiversity. Our results show that increases in green infrastructure have not been sufficient to offset loss of semi-natural habitat, and that landscape links must be functionally effective in order to contribute to grassland diversity.