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