The way the rules are written there is no harder check for multiple people attempting to grapple. Each successful grappler will have the target grappled potentially necessitating multiple athletics checks to escape.
Can you grapple a creature twice?
So as long as your DM agrees that your two grapples are separate ‘effects’, there’s nothing in the rules that seems to prevent you grappling the same creature twice. The creature would need to break each grapple separately (per the rules on PHB. 195 for “Escaping a grapple”).
Does Wildshape break a grapple?
No, wild shape does not automatically break the grapple. Grappling applies the ‘grappled’ condition and conditions are not automatically removed when you wild shape. Further, once you have the grappled condition, the restrictions on grappling target size does not matter.
Can a monster grapple more than one target?
There’s nothing in the Grappled condition that would prevent multiple creatures from grappling a single target. Where it gets complicated, though, is breaking free. From the grapple rules for monsters, we have this: A creature grappled by the monster can use its action to try to escape.
What happens if you grapple more than one creature?
The condition also ends if an effect removes the grappled creature from the reach of the grappler or grappling effect, such as when a creature is hurled away by the thunderwave spell. There’s nothing in the Grappled condition that would prevent multiple creatures from grappling a single target.
How many opponents can you grapple in one round?
Up to four combatants can grapple a single opponent in a given round. Creatures that are one or more size categories smaller than you count for half, creatures that are one size category larger than you count double, and creatures two or more size categories larger count quadruple.
How many weapons can you use while grappling?
Attack Your Opponent: You can make an attack with an unarmed strike, natural weapon, or light weapon against another character you are grappling. You take a –4 penalty on such attacks. You can’t attack with two weapons while grappling, even if both are light weapons.
