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