i believe the problem with this is that OOTP doesn't clear the Starting Pitcher if you sim ahead more than seven days.
In the example above, my rotation is:
1 - F. Gram
2 - O. Wright
3 - M. Jammer
4 - H. Stansel
5 - J. Woods
The seven day lineup is:
Fri 4/21 - M. Jammer
Sat 4/22 - H. Stansel
Sun 4/23 - J. Woods
Mon 4/24 - F. Gram
Tue 4/25 - Off Day
Wed 4/26 - O. Wright
Thu 4/27 - M. Jammer
On Fri 4/28, OOTP should look back in the rotation and select the next starter H. Stansel. Instead it looks back at the seven day lineup and takes the pitcher that schedule to pitch Friday. It's like OOTP should clear the starting pitcher when it clears the lineup but it doesn't.
The work around is to, clear the starting pitchers out. Then OOTP uses your rotation. Or, if you want to use this part of the seven day lineup as it should be, you want to convince your online league to sim seven days at a time.