His heels, verb. phr. (gaming).—The knave of trumps at cribbage or all-fours. Hence ‘two for his heels’ = two points scored (at cribbage) for turning up this card.
1811. Lexicon Balatronicum, s.v.
To tread upon (or to be at or upon) the heels, verb. phr. (colloquial).—To follow close or hard after; to pursue.
1596. Shakspeare, Hamlet, iv., 7. One woe doth tread upon another’s heels.
To go heels over head, verb. phr. (colloquial).—To turn a somersault; to be hasty; to fall violently. Also Top over Tail.
1540. Lyndsay, Satyre of the Thrie Estaitis, 3744. This fals warld is turnit top ouir taill.
To have (or get) the heels of, verb. phr. (old).—To outrun; to get an advantage.
1748. Smollett, Roderick Random. Thou hast got the heels of me already.
Down (or out) at heel, adv. phr. (colloquial).—Slipshod; shabby; in decay.
1605. Shakspeare, King Lear, ii., 2. A good man’s future may grow out at heels.