First thing I suggest is that you force the game to autosave before playing the games against the pirates. To do this, just pause the game and return to the main menu.
As the description says, to get the achievement to pop you must win both of the games against the pirates without using the Skip feature (which means, do not press
).
The first game is the shell game where you need to pick which cup the ball is under twice. The first time the ball is under the cup on the left. The second time the ball is under the top right cup.
The second game requires you to place pieces on the board to block the octopus piece from reaching the edge of the board. Each time you place a piece the octopus will move one spot. To win, you must completely block the octopus piece so it has no where to move.
Unfortunately, the board setup appears to be randomized so I can't give you a step by step guide. However, the good news is there are 2 ways you can go about this:
1) If you're going to lose, you can dashboard and force quit the game. If you forced an autosave like I suggested, then you shouldn't have to redo much.
2) In my case, the octopus escaped and then another board was randomly generated. This board was much easier and I when trapped the octopus the achievement still popped.