I don't really remember many other uphill sprints from Milan (apart from the one Bauhaus won last year), but I'd think with a couple more race days in already Philipsen could have beaten him today. He didn't look that special to me
The first stage he won at Tirreno-Adriatico last year was also uphill, very close between him and Philipsen.
I think today it was the fact Milan did 200m+ in the wind and uphill, Philipsen did about 50m and ran out of legs. Philipsen was better positioned so I agree I think he'd win this stage in July, but straight drag race? Milan takes it.
Edit: there was also actually a stage in last year's Benelux tour, where he beat Philipsen again, which was about 5% uphill, and his win in Saudi in 2022, which was more in the drag category. So, tbf, four wins is pretty good going.