The research was aimed at comparing the formation dynamics of physical, biochemical, and technological characteristics of winter triticale (*Triticosecale Wittm.) grain as compared with wheat (Triticum aestivum L.), and rye (Secale cereale L.). Sampling was carried out at the milky, soft dough, middle dough and hard dough maturation stages, as well as after over-maturation in the field. The growing season of 2017 was cold and rainy, while that of 2018 was rather typical for the Moscow region; in 2019, the hot dry weather changed to the cool one with prolonged rains. In all years, it was raining over the whole grain maturation period. This provided for the evaluation of changes in the studied parameters after overmaturation in the field. Under these conditions, during grain filling and maturation, the mass of 1000 grains gradually increased, and then decreased a little bit due to enzyme-mycosis exhaustion. The grain-unit roughly followed the dynamics of change in the mass of 1000 grains. The highest values of protein and gluten content were obtained at the milky stage, after that their relative content decreased to soft dough ripeness due to the complete accumulation of starch. Afterward, the protein content increased again. This indicates that the processes of enzyme-mycosis exhaustion of grain were going on. It is noteworthy that the lowest activity of enzymes was also observed in hard dough ripeness in all the studied varieties. With further maturation, the autolytic activity increased and reached its maximum at the hard dough (final) maturation stage. Thus, the studied indicators of grain quality reach their maximum values in the middle dough stage, and the delay in harvesting will lead to strong deterioration in the technological properties of grain.