[RPG] How many creatures can attack (melee) a single creature at once (assuming all creatures are medium sized)

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Regarding a hypothetical scenario where you have a party of 8 PC's and one enemy. Can all of those 8 PC's surround and attack the enemy creature (following a square 5×5 feet square grid) in one round?

Another hypothetical scenario where an army of 1000 (all wielding swords) exists. How many members of the army can attack a single creature at once?

Best Answer

If the target is Medium sized and the PC's are medium sized, they can surround and attack it. From the PHB pg 191:

Assuming Medium combatants, eight creatures can fit in a 5-foot radius around another one

Further down on page 192:

In contrast, as many as twenty Medium creatures can surround a Gargantuan one.

This, however is not accounting the fact that creatures can, in the same turn, move closer, attack and retreat (possibly provoking an opportunity attack), leaving room for another to attack in the same round. If you factor that in, depending on the attacker's speed you can fit in far more creatures attacking in the same round.

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