The Legit Solution - Attempt to find a game with four or more players in it (yourself will make five, and yes you DO count as one of the five). Hope that each player in the game (or at least four others plus yourself) will choose any plane that has the letter F next to it's name. Finish in first place, and this achievement will unlock at the end of the game.
The Boosting Method - Gather four other people (or more). Start a Public Match and invite everyone into the game. Any plane pack will work and any any time limit/kill limit as well. I advise you to set the Time Limit as low as possible and the Kill Limit as low as possible. Any map will do. Have each player choose a plane that has the letter F next to it's name. Finish in first place to unlock this achievement at the end of the game.
This achievement is best combined with
The The Oskar achievement in Heroes Over Europe worth 149 pointsUse rockets to destroy 5 enemies on a single life in multiplayer with 5 or more players. and
Choose the plane pack "Rocket Pack". Set the secondary ammo to unlimited, and the kill limit to five. Simply spam the Left Trigger (secondary fire) when you are in range of an enemy plane five times, and the achievements will unlock immediately after the fifth kill.