For the control to turn the pump on after 8 PM and before 2, you'll need to use the OR operator. Or, consider adding an ELSE to the other control:
If Clock Time >= 2 PM AND Clock Time <= 8 PM Pump-1 status Off ELSE Pump-1 status On.
If you're new to WaterCAD/WaterGEMS, I would recommend following the quick start lessons included in the Help documentation. We also have training courses available (see your Bentley Account Manager.)
As a side note, a transient analysis may be warranted when simulating a pump power failure. This can be done using our specialized HAMMER product (training strongly recommended).