The purpose of our research was to expand the genetic diversity and to create the new winter Triticale materials with high grain quality by use of intraspecific and remote hybridization, involving them in the breeding of high-yield cultivars. Samples of winter Triticale were created by intraspecific and remote hybridization methods using multiple individual selections at Uman National University of Horticulture (Ukraine). We created the collection of winter Triticale, which includes more than 300 samples. It consists of unique recombinant forms that differ in morphobiological and economically valuable indicators. The obtained samples were divided according to the plant height into medium-stemmed (over 100 cm), low-stemmed (80–99 cm), short-stemmed (60–79 cm) and dwarf (??60 cm). The sample 68 combined high yield (6.95 t/ha) and grain quality (protein content — 12.8%, gluten — 27.8%, 1000-grain weight — 50.5 g, grain unit — 690 g/l). Sample 83 was characterized by high protein content (14.2%) and gluten (30.2%) of group I, and was up to the standard yield (6.35 t/ha). We created the cultivars of winter Triticale ‘Navarra’ and ‘Strateg’ that listed in the State Register of Plant Cultivars Suitable for Distribution in Ukraine in 2018.