Here’s two prophecies of Isaiah that scholars had a problem with, especially Isaiah 19. If these did not come to pass in the past, they have now.
Syria, the country where the original King of the North was based, would be plunged into a vicious civil war during the latter part of the days. In Is. 17:1 we read of God’s pronouncement against Damascus : “Look! Damascus removed from being a city, and she has become a heap, a decaying ruin.” To me this is a reminder that Biblical prophecies should be taken seriously.
In connection with Egypt of Is. 19:1-15, Ringgren of TDOT, vol. VIII, p. 529, had the following to say:
The series of statements in Is. 19:1-15 is more problematical, and its authenticity is generally disputed based on stylistic considerations. A prediction is made for the dissolution of national order, the collapse of economic life, and the confusion of Egypt’s rulers. “A fierce king will rule over them” (v. 4: historical allusion or a prediction for the future?). Isaiah’s usual warning against reliance on Egyptian aid is absent. These assertians are followed by a series of statements introduced by bayyôm hahû’ [an eschatological marker] which are doubtlessly secondary….
As seen, a historical fit for Is. 19 would cause both exegete and interpreter untold problems. Such a period in Egyptian history cannot be identified. However, above statements would make perfect sense as a prediction for the future, as of now.