In the early years of the O Street Market, German women and men constituted a large percentage of the sellers. After World War II, African American sellers began to predominate, occupying small stands within the large market space. The market had become of the primary shopping venues for Shaw residents. In the 1960s it had deterioriated, in part because of the increasing competition from modern grocery stores. Because residents relied on the food sold at the market, they picketed the market and demanded successfully that the city clean it up.

During the 1968 riot/rebellion, the market temporarily closed. When it reopened again in 1980, the United House of Prayer's gospel brass band played during the celebration. The reopening of the market also signaled a revitalization of the area, which brought a Giant Food supermarket next door.

The O Street Market was empty and about to undergo renovation in 2003 when a major snowstorm collapsed the roof and structure, leaving a partial façade.