FWIW, not all retailers that are accepting EMV credit are currently setup to accept EMV debit. So just because you dip for credit cards in a store doesn't necessarily mean you also dip with debit cards.
Chase specifically tells its customers with EMV debit cards to swipe them first, and only dip them if instructed.
Don't forget, Apple Pay uses a token, which is a completely different card number. Even if you had your physical card with you, the last four of that wouldn't match what Apple Pay sent.
Yeah, I did that this morning using the Walgreen's iOS app. Well, I guess that's not exactly entering the details into Apple Wallet directly, but I was able to type the number into the Walgreens app, which put the card into the wallet.