watchOS 7 has to be the first watchOS to abandon a big portion of the Apple Watch install base. Previously watchOS 5 abandoned the first generation Apple Watches, also known as the Series 0, but the number of iPhone users who owned these first generation rarities is pretty small. Apple Watch really started becoming more popular during the Series 2’s life cycle, as the software started to be more refined, as well as the introduction of the Series 1 as a lower entry price point for the Apple Watch ecosystem. The Series 1 stayed in the lineup until the introduction of the Series 4, so it will not be surprising if a lot of Apple Watch owners, especially older ones, are still rocking them.

It is unfortunately not easy to find an answer to the above question (in the title) as Apple support documents don’t offer a clear answer, and many self-proclaimed experts on the interwebs mostly state something along the lines of “iOS 14 only supports watchOS 7” or “watchOS 6 is not supported on iOS 14”. Many of these people likely have not tried to pair (or re-pair) a Series 0-2 to iOS 14. We know that if you already have the Series 2 paired to your phone before you update to iOS 14, it will continue to work after the update. But what most don’t know is if you unpair that Series 2, will it be bricked forever unless you somehow downgrade to iOS 13? (It won’t be)

Well, the answer to the question in the title is YES. You can pair the Series 2, the Series 1 and likely the Series 0 (first generation) Apple Watch to any iPhone with iOS 14 (will try and report back if anyone is interested).

I have personally just finished unpairing and re-pairing my Series 2 (on watchOS 6) from a 8 Plus to the Xs Max, both on iOS 14, and there is no reason why the Series 1 won’t work.

I did notice something different during the pairing process, the watch will ask to enter your account password on the watch itself, and the process itself is a bit wonky compared to pairing my watchOS 7 Apple Watches, not sure if it has anything to do with pairing watchOS 6 to iOS 14 or if it was just a bug.

Nevertheless, if you are wondering about the exact same question, you now have your answer.