Let's see, about the cutlass:
https://aqwwiki.wikido*****m/pie-rate-...cutlass-5-2014
The item went rare, so you wont drop it from Undead Pirate
I don't know what are you trying to get from Red Dragon. It might be just bad luck.
For example: While I just trying to get Dark FrostSpawn Mage(A 1% drop rate), first I got like 5 Treasure Chests(0.75% drop rate)