it depend on yr arvl time if arvl a bit early at around 1500lt, then it should be okay.
Due to if his flt at 2359Lt, he should arvl at airport at around 2159 at least.
That mean he have to leave fm ship at 1930Lt. which your good vsl still not all fast yet (base on arrive 1800Lt).
Again need to have some time for immigration for entering formality before he leaving.
It seem very risky to leaving with this flight on 5th.