Here's the sequence of events:
Midweek rollover. Next game auto-scheduled for 8am the following day.
Admin changes rollover time to an hour later. This doesn't change the schedule.
Game rollover. Next midweek auto-scheduled for 9am the same day.
Admin pushes next game out by a day to resynchronise with schedule.
So yes, we had 2 rollovers in 2 hours. After the game had run the system looked for the next 9am available and found it was 59 minutes later, rather than 24 hours 59 minutes, which is what was expected.