I have the non expandable version of this bag.

As long as its not completely, about to burst open, packed, there should be no issue fitting it on either of these planes. I know because I've done it before, as well as on just about every DL, CO, and NW flight I've taken over the past few years (aside from regional jets where nothing fits). Shockingly, I was even able to squeeze it into the luggage sizer at LHR security after removing a couple of items. So, even packed very fully, you should still be able to squeeze it in. I go wheels out, never tried it the other way.

On the 2 seat side for the MD-88, you'll have to turn it sideways, but you'd have to do that for any piece of luggage. The only issue I can think of is making sure you're mindful of any protrusions (hinges, etc.) in the bin, but again, this would be the same with any bag.