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A Grapple is performed by:

you try to seize the target by making a grapple check instead of an attack roll: a Strength (Athletics) check contested by the target’s Strength (Athletics) or Dexterity (Acrobatics) check (the target chooses the ability to use).

So, if I gather correctly, a contest is an Athletics check from the Grappler against an Athletics/Acrobatics check from the Grappled. What if the values tie? Who wins?

To free yourself from 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.

In this situation, if the checks tie, who wins?

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  • \$\begingroup\$ This is exactly the same as any other check in the game. If you roll higher, the thing happens. If it's a tie or lower, the thing doesn't happen. The fact that the roll is contested doesn't change anything. \$\endgroup\$ – Mooing Duck Jan 12 '18 at 22:08
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    \$\begingroup\$ @MooingDuck An attack roll that matches AC lands. A Saving Throw that matches the DC succeeds. So it's not quite the same \$\endgroup\$ – BlueMoon93 Jan 13 '18 at 9:50
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Tie results in status quo

See contest rules in Player's Handbook, page 174:

If the contest results in a tie, the situation remains the same as it was before the contest. Thus, one contestant might win the contest by default.

This means a grappler loses the tie when making a new grapple, as before the contest the target isn't grappled, but wins ties when an already grappled target is trying to escape (as before the target is grappled before the contest).

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