You can get this achievement during the mission where you play as the american and you drive a tank while you protect your army buddies that follow you. You can find this mission in chapter select, Ch. 3: The Somme.
There are two things things that will help you immensely against those pesky planes that seek to extinguish the life out of your men:
1. Always aim your cannon at as high of an angle you can
2. Spam the fire button the whole time (especially during the second trip and you will be fine)
There are a few tricky bits during the first trip, where you might be driving down a hill when a planes comes and wipes out some of your men. Just remember when you see an alert of a plane coming, stay on an upwards incline or even terrain to destroy the planes.
During the second trip, just keep moving forward and spam the fire button. The achievement should unlock once you meet another tank after this.
There are five men during the first trip (if you save all five two of them will also drop collectibles, courtesy of b0seiju) , and four in the second, so if you are missing one, quit and restart the mission.