Know that all monitors are not made equal. They have different panels, screen types, resolutions, etc. The quality of the hardware used inside the monitors changes from brand to brand even though they may have the same specs on the paper. Some Old monitors using a VGA connector might not even support overclocking. The latest monitors tend to overclock better.
Most importantly, check your panel specs. Many monitors that run at 144Hz use 120Hz panels. Some monitors running at 165Hz use 144Hz panels and few monitors running at 75Hz use 60Hz panels. They are generally overclocked by the manufacturer. It would be harmful to add an overclock on top of an already overclocked monitor.
Also, in some cases, when you try to overclock two monitors of the same brand, model number etc., you may not be able to achieve the same results on both of them.
For example, if you overclock one monitor to 75Hz from 60Hz, the other monitor may only be overclocked to 70Hz. This is not to say that the monitor that achieved a less powerful overclock is a defective one.
In most of the cases, the video scalers used in the monitors restrict the capacity up to which you can overclock. This is to prevent damage. The ability to which you can overclock also depends on the silicon lottery of the hardware used on which you have no control over.
The connectors you use and the resolution of the monitors also come into play. Monitors using display port and dual-link DVI connectors tend to overclock better than those using a single DVI cable or an HDMI cable. Use G-Sync and Free Sync monitors for better gaming experience and reduced stutter and tear.