Morningglories (Ipomoea spp.) are among the most troublesome weeds in cucurbits in the United States; however, little is known about Ipomoea spp. interference with horticultural crops. Two additive design field studies were conducted in 2020 at two locations in Indiana to investigate the interference of ivyleaf morningglory (Ipomoea hederacea Jacq.), entireleaf morningglory (Ipomoea hederacea Jacq. var. integriuscula A. Gray.), and pitted morningglory (Ipomoea lacunosa L.) with triploid watermelon [Citrullus lanatus (Thunb.) Matsum. & Nakai]. Immediately after watermelon was transplanted, Ipomoea spp. seedlings were transplanted into the watermelon planting holes at densities of 0 (weed-free control), 3, 6, 12, 18, and 24 plants 27 m−2. Fruit was harvested once a week for 4 wk, and each fruit was classified as marketable (≥4 kg) or non-marketable (<4 kg). At 1 wk after the final harvest, aboveground biomass samples were collected from 1 m2 per plot and oven-dried to obtain watermelon and Ipomoea spp. dry weight. Seed capsules and the number of seeds in 15 capsules were counted from the biomass sample to estimate seed production. Ipomoea spp. densities increasing from 3 to 24 plants 27 m−2 increased marketable watermelon yield loss from 58% to 99%, reduced marketable watermelon fruit number 49% to 98%, reduced individual watermelon fruit weight 17% to 45%, and reduced watermelon aboveground biomass 83% to 94%. Ipomoea spp. seed production ranged from 549 to 7,746 seeds m−2, greatly increasing the weed seedbank. Ipomoea spp. hindered harvest due to their vines wrapping around watermelon fruits. The most likely reason for watermelon yield loss was interference with light and consequently less dry matter being partitioned into fruit development due to less photosynthesis. Yield loss was attributed to fewer fruits and the weight of each fruit.