Little Snitch: Does restricting address/port for an application disable future connection prompts?
If you click Deny on the picture you posted, then no further notifications will be shown [&amp; the connection will be denied] for gamed trying to connect to (static.gc.apple.com AND port 443), not for (static.gc.apple.com OR port 443).

Any &amp; all other connection attempts will be flagged - e.g. a connection to static.gc.apple.com on port 442 would be flagged, or a connection to notstatic.gc.apple.com on post 443 would be flagged.

The next time gamed was launched, your previous deny would again be flagged for your attention, as you only denied it until Quit.

Note:
If you click on the static.gc.apple.com in the line above, you can broaden the domain you wish to block - though it must be said that blocking Apple devices &amp; services [gamed is an Apple service] from connecting to Apple is not really going to be a good move, long-term.
In general terms, Little Snitch can be used to block any or all connections for any app or service -  as either a precision tool or a sledgehammer!
It should be used with care.