More widespread introduction of winter triticale (xTriticosecale Wittmack) could increase the sustainability of Northern U.S. crop and livestock systems by reducing soil erosion and nitrate loss to ground and surface waters. However, the fall planting window for maximum winter triticale grain yields in Iowa is typically only two to three weeks because it is planted after harvest of summer annuals. One solution to expanding the planting window is to identify and select triticale genotypes with resilience to late planting. An experiment was conducted at three Iowa locations to determine the response of commercially available winter triticale genotypes to early and late planting dates. Twelve winter triticale cultivars and one wheat cultivar were planted on two different planting dates, late September and mid October, at each location in 2004-05 and 2005-06. Grain yield varied with location, year, and planting date indicating cultivar performance was highly situation specific. The grain yield of cv. NE426GT was statistically significantly superior to all other cultivars under both early and late planting. Planting in mid October when compared to late September resulted in less grain yield in central and northern Iowa, but not southern Iowa. Losses from late planting were as great as 29% in northern Iowa. Spikes m^-2 decreased from 469 to 393 and kernels spike^-1 increased from 35.9 to 39.4 as planting was delayed. There was a close positive relationship between grain yield from early planting and grain yield from late planting. Winter triticale cultivars with high grain yields and resiliency to late planting had larger fall plant weights, fewer kernels spike^-1, and larger kernel weights than winter triticale cultivars with smaller plants in the fall, more kernels spike^-1, and smaller kernels weights. These traits could be used to improve winter triticale grain yields and late planting tolerance.