Parallel declines in insect-pollinated plants and their pollinators have been reported as a result of agricultural intensification. Intensive arable plant communities have previously been shown to contain higher proportions of self-pollinated plants compared to natural or semi-natural plant communities. Though intensive grasslands are widespread, it is not known whether they show similar patterns to arable systems nor whether local and/or landscape factors are influential. We investigated plant community composition in 10 pairs of organic and conventional dairy farms across Ireland in relation to the local and landscape context. Relationships between plant groups and local factors (farming system, position in field and soil parameters) and landscape factors (e.g. landscape complexity) were investigated. The percentage cover of unimproved grassland was used as an inverse predictor of landscape complexity, as it was negatively correlated with habitat-type diversity. Intensive grasslands (organic and conventional) contained more insect-pollinated forbs than non-insect pollinated forbs. Organic field centres contained more insect-pollinated forbs than conventional field centres. Insect-pollinated forb richness in field edges (but not field centres) increased with increasing landscape complexity (% unimproved grassland) within 1, 3, 4 and 5 km radii around sites, whereas non-insect pollinated forb richness was unrelated to landscape complexity. Pollination systems within intensive grassland communities may be different from those in arable systems. Our results indicate that organic management increases plant richness in field centres, but that landscape complexity exerts strong influences in both organic and conventional field edges. Insect-pollinated forb richness, unlike that for non-insect pollinated forbs, showed positive relationships to landscape complexity reflecting what has been documented for bees and other pollinators. The insect-pollinated forbs, their pollinators and landscape context are clearly linked. This needs to be taken into account when managing and conserving insect-pollinated plant and pollinator communities.