The region where Yellow and Huai Rivers met the Grand Canal became a key location for water regulation because of the opening of Grand Canal in Ming Dynasty. Regulation procedures implemented by the government, aiming to keep the Grand Canal unimpeded to navigation, facilitated the evolution of river system structures and water regimen. In early Ming Dynasty, the configuration of river channels was similar to that in Yuan Dynasty, following a pattern of parallel flows with interchangeable main and tributary channels. As the Grand Canal, Huai River and Yellow River were under regulation, and especially as levees were constructed, channels of Yellow River went through a concentration process. They firstly merged from a regional network pattern into a linear pattern, and then continued converging towards a point at Qingkou. The first stage of this process was the abandonment of the northern branch of Yellow River, while the second stage was lining the Xu-Pi segment of Yellow River up with the upper stream. After flow directions of channels were fixed into the Xu-Pi segment, most levee failure events during the Reign of Jiajing Emperor occurred upstream to Xuzhou, but after the 44th year of Reign of Jiajing Emperor, most of such events occurred downstream to Xuzhou. The channel regulation near where Yellow River and Grand Canal meet started with a broader, fan-shaped target region extended from south to north, and then reduced to the southern half of the fan-shaped region, and then concentrated to a linear belt and eventually to Qingkou. The regulation generally served for maintaining the navigational condition of channels. From a regional channel network to a point, or from a broader region to a smaller region and eventually to a single point, such kind of engineering process marked the characteristic of how Ming Dynasty conducted hydrological regulation projects in the region where Yellow and Huai Rivers met the Grand Canal. This hydrological regulation process that follows the change of water environment accordingly fully reflected the wisdom of ancient people in utilizing the aquatic environment on a large regional scale. It has remarkable ecological characteristics.