This is cumulative across all MP games, but can only be earned in multiplayer. Ensure that you have an airfield (any medium or large Island Capture map), open the Support Manager (press Z) and choose your air base. Launch fighters until you run out of Command Points, then cycle through all of your launched fighters telling them to land (press ALT and click in the right quadrant). Rinse and repeat until the achievement unlocks. You can also manually crash your planes if you don't want to wait for them to land.