@Graeme **********
,
You already got possible answers based on the information you provided. It may or may not help your friend as there seems to be lack of concrete information. This is the reason why this group doesn't do "for a friend" posts usually.
Have your friend post on his own if he needs further or clear advice. Or you post further questions for him with photos of all related stamps on his passport, so that this group can provide legit advice.