Grain morphometry is presently among the main targets of modern barley breeding. Three yield trials with winter barley cultivars were performed in the 2018-2020 period at the National Agricultural Research and Development Institute Fundulea in order to analyze the weight of thousand grains and grain morphometry (grain length, grain width, grain area, grain circularity, grain length-width ratio, and factor form density) of six and two-row registered Romanian winter barley cultivars. Acquired image analysis of grains produced by 25 winter barley cultivars in three years with different grain filling conditions, showed that variation of climatic conditions significantly influenced the thousand grain weight (TGW), grain length (Gl), grain width (Gw), grain area (Ga), grain circularity (Gc), grain length-width ratio (L/W ratio) and factor form density (FFD). The barley cultivars were significantly different for all studied traits, which underlined a high level of diversity. All traits were on average different between six-row and two barley cultivars. TGW was highly correlated to Ga, Gw, and FFD. The PCA analysis revealed that PC1, PC2, and PC3 explain 99.1% of the amount of variation. Our paper provides extended information and the newest grain morphometry insight of an old, oldest, and modern barley germplasm released in three different breeding periods.