«Which ones are correct? (if you ask my opinion first, I have no idea)»
Why're you asking then? Bare answers will scarcely help you understand English tenses! Go read about the subject in grammar books and then ask about what you haven't got...
Here's my try:
1 — C.
2 — A, C, D.
(hope someone corrects me :)
EDIT: Using "when" in #1 will bear the meaning that he won all the five awards the year he turned 23, which is technically correct but unlikely.