Notes:

Image in question:

To which I just added 4 more panels.

1940s: Unnamed Dragon (The Reluctant Dragon)
1950s: Maleficent (Sleeping Beauty; the movie came out in early 1959, but it still counts.)
1960s: King Ghidorah (Ghidorah, the Three-Headed Monster; because Godzilla technically isn’t a dragon.)
1970s: Elliott (Pete’s Dragon)
1980s: Falkor (The Neverending Story)
1990s: [Left] Dragonite (Pokemon; because Charizard wasn’t a dragon yet), [Right] Mushu (Mulan)
2000s: [Left] Cassie (Dragon Tales), [Right] Jake Long (American Dragon: Jake Long)
2010s: [Left] Toothless (How to Train Your Dragon), [Middle] Smaug (The Hobbit), [Right] Spike (My Little Pony: Friendship is Magic.)
UPDATE:
2012: Anna (Fire Emblem: Awakening)
2014: Ugin, The Spirit Dragon (Magic: The Gathering)
2016: Corrin (Fire Emblem Fates)
2017: Tohru, Kanna Kamui, Elma, Quetzalcoatl and Fafnir (entry you are in right now).

And yes, I know the manga is from 2013, technically making this older, but the anime aired on 2017, so, good enough. Other characters here have the same pick to them. No need to be dense about how "accurate" this is.