Spoiler alert: Gerrit Cole won't actually be making two starts.
I rank him here because he's currently projected to, but Week 27 (Sept. 23-29) is of course the final week of regular season. And playoff-bound teams typically use the final week of the regular season to set up their starting rotations for the playoffs, which generally means building in some rest for their best starting pitchers at the end of the week.
Now, it's possible he makes a tuneup start of two innings or so in lieu of a side session. But it'd be negligent of the Astros coaching staff to leave him out there for a full six innings next Sunday. Chances are higher they skip him altogether.
Naturally, I still rank him high here because ... he's Gerrit Cole. One start or two, you're obviously not benching him, and the same goes for Mike Clevinger and Max Scherzer if the Indians and Nationals are secure enough with their postseason outlook to skip them at week's end. Jake Odorizzi wouldn't be as obvious of a one-start choice if the Twins elect to skip him, but he has been pitching well of late and will be facing the Tigers at the start of the week. Patrick Corbin, meanwhile, seems like a relatively safe bet to make two starts given that he'd be only the Nationals' No. 3 pitcher in the playoffs.
Of course, no bet is safe, really, when playing the pitching probables game in the final week of the regular season. Even the teams that aren't playoff bound are liable to skip a pitcher willy nilly just to give some kid a thrill before shutting down shop, so if you're eyeballing a two-start sleeper, you better be comfortable with him potentially making only one start. Dinelson Lamet seems the likeliest of those owned in less than 80 percent of CBS Sports leagues to deliver something worthwhile, even with a difficult matchup. The Tommy John returnee is coming off a 14-strikeout effort at Milwaukee and has had an elite swinging strike rate across 13 starts.