Waiting for Dublin (2007)

On New Year's Eve 1944, American pilot Mike Clarke inadvertently bets Al Capone's nephew $10,000.00 that he can shoot down five enemy aircraft. Later, forced to land near a remote village in Ireland after running out of fuel, Mike learns that he is cut off from the rest of the world with no way to rejoin the war and shoot down his fifth plane, which is the only way he can win the bet and save his own life. With nowhere to go, he eventually befriends the colorful villagers and meets a fiery red-head named Maggie who shows this pilot that combat can take place on the ground just as well as in the air. It doesn't take long for Mike and Maggie to grow close as she helps him figure out how to win his bet while winning her heart in the process

Unfortunately the movie Waiting for Dublin is not yet available on HBO Max.