Understanding the changes in phenotype resulting from the selection pressure and agronomic adaptation of grain yield provide an indication of the pathways for future increases in grain yield. Six dry land representative winter wheat cultivars (Triticum aestivum L.) released from 1942 to 2004 in the Loess Plateau of China were investigated to determine how the yield components of winter wheat were associated with grain yield at the Changwu Agricultural Research Station during the 2011 - 2012 and 2012 - 2013 seasons, using a completely randomized block design with three replicates. Plant height, aboveground biomass, grain yield, and yield components were measured, together with the traits of superior and inferior grains and the pre-anthesis stored dry matter remobilized to the grain was determined. In the relatively wet 2011 - 2012 season, there was a significant increase in grain yield and aboveground biomass with the year of release, but not in the dry 2012 - 2013 season. The harvest index (HI) and average grain weight (AGW) increased significantly with the year of release in both cropping seasons. HI and AGW are likely potential traits for improving grain yield of winter wheat in the Loess Plateau. The increase in HI mainly resulted from the decrease in plant height, and the increase in the use of pre-anthesis stored assimilates for grain filling. The increase in AGW mainly resulted from the increase in the proportion of superior grain (SG) and the decrease in the proportion of inferior grain (IG) in the whole spike in both cropping seasons. Depending on the climatic conditions, the different winter wheat cultivars showed different ability to use pre-anthesis stored assimilates. Modern wheat cultivars had higher yield under different rainfall conditions, and high ability to use pre-anthesis stored assimilates to fill the grain than earlier released cultivars. Both, the increase in sink capacity and source availability, should be considered as a strategy for increasing future grain yield in Loess Plateau of China.