Thank you for the great explanation giorginho . It is indeed the case that:

1. My card renewal date doesn't match upgrade tier date just like in your screenshot (which is not part of the inquiry), and,
2. I had a flight on 1 July 2024

For me, the confusion also stems from the same "12-month period" used in Aegean Pass, in which my pass is valid from 01/01/2025 to 01/01/2026 (inclusive). if this is consistent, then Aegen doesn't count the last date, and I have up to inclusively 1 July 2025 to qualify.

The problem is Aegean doesn't have daily flight from DUB so I couldn't move my trip earlier. I sent them an email and let's see what they say.