in a python console on a windows machine:

import datetime
d = datetime.datetime.fromtimestamp(0)
d
>datetime.datetime(1969, 12, 31, 19, 0)
d.timestamp()
>OSError: [Errno 22] Invalid argument

on a macOS machine : 

d = datetime.datetime.fromtimestamp(-1)
d
>datetime.datetime(1969, 12, 31, 19, 0)
d.timestamp()
>-1.0

both machines running 3.6.9

I would expect them have the same behaviour.