This achievement is very difficult to rig through normal play except on particular campaign levels with weaker characters or on lower difficulties. One such example is Star Breaker's fourth campaign level, map Farm with QP (Dangerous), Sora (Military), and Aru. The nature of the map stalls the CPU from normas, keeps them running in circles and thus easier to chase/lure, and its small size helps you hit them with your bombs, since unlike Krilalaris's hyper, map size has no bearing on number of bombs placed. It is recommended to play on Easy difficulty to nerf their rolls a little and keep them from getting a lead before you can achieve 50 damage.
It is also reportedly achievable in multiplayer, on small maps with avoidable bases like Clover, Farm, or Vortex, and just so long as everyone is cooperating. Flying Castle is a good choice for those boosting, with its unprecedented 8 hp making the 50 damage achievable in, at best, 6 bombs.