One last clue and I'll give you all the answer:
1) These two aircraft shared a distinction from all other aircraft
2) While both types had great combat records, one was the first and the other the last
3) The two aircraft had maiden flights approximately four years apart
4) The two aircraft made their first combat flights approximately nine years apart
5) The two aircraft were involved in events that led to the loss of the first but not the second
6) Only the aircraft that was lost had more than one person on board.
7) The "last" aircraft was performing a function it was never designed to perform
8) The "last" aircraft was replaced soon after by new, faster aircraft that were themselves in service for well over 30 years
9) The last of the "first" was retired by the air forces of the building nation after only eight years of service
10) Both the "first" and the "last" had a disadvantage in their similar events, the "first" wasn't able to overcome this while the "last" did
11) The aircraft involved all used different engines
12) All aircraft involved were armed with either machine guns or cannons, no missiles
13) The "first" and "last" flyers spoke the same language, more or less, while everyone else involved spoke their own
14) The events started by the "first"(resulting in it's crash landing afterward) and ended with the "last" covered three major conflicts involving the nation that manufactured the "last"
15) The "first" used a radical construction(for the time it was designed) that the powers that be didn't really trust or want to buy at first while the "last" was designed and used to do the same tasks as three well known, front line, proven combat aircraft that it replaced
16) The "first" was this country's first aircraft to top the 400 MPH mark while the "last" was the last not to make 400 for it's country,even though it had more power than many that could
17) Both aircraft were designed during the same conflict, the "first" participated while the "last" waited for the next where it did not fly in defense of it's own country but to protect troops from it
Good Luck