Granted entry is when you cross the border. So they have status when they cross.
In terms of PR + OWP: if you apply before the IEC expires for visitor status, he had implied status as a visitor... So as long as you have done that, and you can show you sent it (online they will already know, if you sent paper, include a courier receipt), and you can also mention it on IMM 0008 if they return the app (applied for visitor status after IEC and the date applied).
Important to note that, if his status somehow runs out, he can still apply for a PR inland, but no OWP until they tell him he is eligible (AIP). So worst case, he applies as out of status. There is a few cases here that did that, and most are still successful.