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