Score
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Best
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Add cards to a running total that must stay under ninety-nine, and spend your escape cards at the right moment.
You and the rival take turns adding one card to a running total. A card that would push the total past ninety-nine cannot be played, and whoever has no playable card left loses the round. Most cards simply add their own number, but four of them behave differently: a nine leaves the total exactly where it is, a ten can be plus ten or minus ten, a king slams the total straight to ninety-nine, and a four skips the rival so you play again. You start with three lives; every round you lose costs one. Win a round and the next one starts at a higher total, and past a point you hold fewer cards as well. Your score is the number of rounds you win.
Four cards decide this game and the rest are just arithmetic. The nine, the ten, the king and the four are your escapes, and the entire skill of Ninety-Nine is knowing when to spend one. Everything else in your hand only ever pushes the total closer to the cliff.
The ten is the rarest thing in the deck: the only card that walks the total backwards. Playing it at plus ten while the total is still in the twenties is throwing away a parachute you will badly want at ninety-one. Hold it, and hold the nine with it, because a nine is a free turn at any total whatsoever — it is worth the most precisely when nothing else in your hand is playable.
The king is not a defensive card, it is a punch. It sets the total to ninety-nine and hands the rival a position where only a nine, a ten or a four saves them. Fire it when the total is already high and the rival has just drawn, and it very often ends the round on the spot. Firing it early is close to wasting a turn, because you have handed yourself the same cliff you meant to build for them.
The four is the quiet one. Skipping the rival means you play twice in a row, which is how you dump a dangerous high card and still keep the escape you were saving. Measured across thousands of rounds, a player who saves escape cards for a high total wins about half again as many rounds as one who plays whatever comes to hand, and more than twice as many as one who burns escapes the moment they arrive. That gap is the whole game, and it only widens as the rounds start higher and your hand gets smaller.