Timeline is a card game played using 110 cards. Each card depicts a historical event on both sides, with the year in which that event occurred on only one side. Players take turns placing a card from their hand in a row on the table. After placing the card, the player reveals the date on it. If the card was placed correctly with the date in chronological order with all other cards on the table, the card stays in place; otherwise the card is removed from play and the player takes another card from the deck.

The first player to get rid of all his cards by placing them correctly wins. If multiple players go out in the same round, then everyone else is eliminated from play and each of those players are dealt one more card for another round of play. If only one player has no cards after a bonus round, he wins; otherwise play continues until a single player goes out.

Timeline Challenge incorporates the original mechanic of the series into progressive game track, of which players can move between 0-4 spaces per turn. Players will have to make use of pre-determined time periods and guess where the incident depicted on the card occurred. There are four different challenges, and they are played depending on the color of the game space of the lead player. Additionally there are two further challenges which allow the two players at the back of the pack to catch up. Although the game comes with its own cards, it can be integrated with any or all of the previous sets.