PlayIt Live will schedule items in the first clock that is scheduled for that hour, so will ignore the second one you added. You can right click the Auto DJ clock in a hour and click Delete and select Only This Occurrence. It will remove that occurrence from overall recurring item allowing your individual clock to be used.
I am making my first clock schedule and I'm not sure I'm doing it correctly. I have made a general auto DJ clock which I have scheduled to all hours in the week. I am then creating individual clocks for recorded shows. When I try to schedule these in the hour that I want them to play it looks as if the hour is split between the autodj clock and the show clock (see the attched screenshot). How do I set it to overwrite the autodj clock with a show clock if I schedule it for an hour already occupied by an autofj clock?