If they lose every game between now and then, the White Sox will break the modern era losing streak record on September 17 and the overall losing streak record on September 21. The toughest obstacles the team faces in achieving these milestones are random chance creating a win and right before they would start setting the records, they play 6 games against the 2 worst teams in the AL besides the White Sox, the A's and the Angels. If they lose every game between now and the A's series, they'll have a 19 game losing streak heading into the series.