Yes, it does make a difference. If the Brewers win today and lose tomorrow, they are either 5 or 6 games up. If they lose today and win tomorrow, they are either 4 or 5 games up. Today's game counts twice as much in the standings (assuming Pittsburgh is not a threat to win the division). But this is all speculation whether the Cubs will be a threat to win the division or not. With Baez, Rizzo, Bryant heading into free agency and Kimbrel with a 16 million club option for 2022, the Cubs have 30 days to decide if they are in or out, because they simply are not going to let those three (probably four) players walk with no compensation. To that end, one game in the standings isn't going to make the Cubs buyers, or stand pat as opposed to selling.