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The spell Bigby's Hand creates a large hand of force that can grapple a target:

Grasping Hand. The hand attempts to grapple a Huge or smaller creature within 5 feet of it. You use the hand's Strength score to resolve the grapple. If the target is Medium or smaller, you have advantage on the check. While the hand is grappling the target, you can use a bonus action to have the hand crush it. When you do so, the target takes bludgeoning damage equal to 2d6 + your spellcasting ability modifier.

Once grappled by the hand, a creature can attempt to escape the grapple using the general rules:

Escaping a Grapple: A Grappled creature can use its action to Escape. To do so, it must succeed on a Strength (Athletics) or Dexterity (Acrobatics) check contested by your Strength (Athletics) check.

Bigby's Hand has advantage when initiating the original grapple. However, does it also have advantage on contested checks when the grappled creature attempts to break free of the grapple?

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Yes.

The description says:

You use the hand's Strength score to resolve the grapple. If the target is Medium or smaller, you have advantage on the check.

Resolving the grapple means to compare the attacker's Strength check and the Strength check of the target. Since these checks are done either

  • on the first attack, when the attacker tries to grapple the target
  • subsequently, when (and if) the target tries to escape from the grapple

the Bigby's Hand has advantage both on the initial attack and on subsequent contested checks related to target's escapes, provided that the size requirement is satisfied.

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