Here is the full list of all 20 Poker Night at the Inventory achievements. It takes around 20-25 hours to unlock all of the achievements on Windows.
Win a game on hard.
Knock out The Heavy after he's bought in with his special item.
Knock out Strong Bad after he's bought in with his special item.
Knock out Max after he's bought in with his special item.
Win consecutive all-ins.
Win three straight pots.
Knock out Tycho after he's bought in with his special item.
Win a pot with two or more opponents when you are all in.
Win a hand with a Straight Flush.
Win a hand with Four of a Kind.
Check a pat hand.
Win a hand with a Flush.
Win 12 or more hands.
Win a hand with a Full House.
Win a hand when you have three of a kind comprised of three kings (of any suit).
Win a full game.
Win a showdown where you and the opponent have same hand (pair or better) and you have a better kicker.
Win a showdown with just a high card.
Win a hand with a Straight.
Win a hand with a 6 card and a 9 card of any suit.