Tall fescue [Schedonorus arundinaceus (Schreb.) Dumort.] is a common grass species in the eastern half of the USA, but legumes grown with it could provide benefits. Obstacles to legume establishment in fescue pastures include disease, insect damage, and grass competition. Experiments were performed in 2010 and 2011 at Site 1 to test the efficacy of insect control, disease control, and two methods of grass suppression on seedling establishment of three legumes. The highest seedling density of red clover (Trifolium pretense L.) was obtained with glyphosate treatment regardless of pest control and for clipping without pest control. No overall or consistent benefit was found for white clover (Trifolium pretense L.) or trefoil (Lotus corniculatus L.) from seed and foliar insecticides or fungicides, or for grass suppression by either clipping or glyphosate application. Experiments were performed in 2012 and 2013 at Site 2 to test the efficacy of grass suppression by grazing cattle or by clethodim application. Seedling density of red clover was not significantly improved by either treatment, but the density of birdsfoot trefoil was increased by clethodim, and the density of white clover was increased in 2013 by both methods of grass suppression. Overall, red clover was least sensitive to grass competition. Birdsfoot trefoil was better served by the immediate effect of chemical suppression, whereas white clover benefitted most from the lengthier grass suppression provided by grazing.