I think the Sox would not beat the Jays, Tigers, Astros or Mariners in a playoff series. Rangers are on a 10-2 run. There's a good chance they push the Sox out of the playoff position for good by the time the deadline comes anyway. Sox best chance is for the Yankees to free fall.
The reason winning pretty matters is because ugly baseball doesn't win in the playoffs. The bad baseball that gets the Sox by during the regular season won't work in October for long.