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