HK attacks are per ship or plane. . .so, if you have three destroyers, you get three dice (needing a 1).
Convoy or fleet ASW is different. You add up the total number of points you have defensing the convoy and roll on a table against every sub attacking the convoy. So: if two subs are attacking the convoy, you would roll 2 dice to defend the convoy.
Each destroyer / plane can either be HK or be assigned convoy escort - ships don't get to attack twice. So, as the Allied player, you need to decide if your destroyer is going to be off chasing subs and attack once with its HK # needed to kill or is going to sit back and escort the convoy and defend on the ASW table.