Drilling glass for big bulkheads a few ?s

[Hustler]

I need to drill for 2 2" bulkheads in my sump.
It currently has a 1 1/2" bulkhead where i need to have a 2" can I drill over that hole seeing as its a larger diamond holesaw bit? Ide drilled plenty of larger holes in 1/2 and 5/8s glass but ive never re drilled in the same spot...
I may also have to drill in place so the glass will be verticle.... Im thinking ill use the putty with a half cut tupperware dish so its half submerged and I can pour water over the top aswell..... anyone ever tried this method? or have a better one lol
It always takes me a few beer to try and punch through glass..... this job will be worse on the nerves for sure