Headline Chasers was played in three rounds, referred to on-air as "editions" by Martindale in keeping with the newspaper theme of the program.

Either couple could buzz-in at any time and guess; a correct answer won the money at stake, while a miss gave the opponents a choice between trying to solve it immediately or waiting for additional clues and letters.

During the second edition, the couples attempted to identify the subjects of magazine covers and video clips, which were purposely distorted in some way.

For the video questions, the clips would be scrambled to start and would slowly come into focus while the audio could be heard without distortion.

The value of each puzzle began at $500 and decreased by $100 for each revealed clue (magazine covers) or for every few seconds that no one buzzed-in (video clips).

If a couple buzzed-in and could not identify the subject, the value was frozen and the opponents received any remaining clues or could see the entire clip before making their guess.

The couple in the lead following the final question won the game and moved on to the bonus round, and both teams kept their winnings.

A couple could win up to $23,600 in a single game, by solving every headline/cover/video clip for its maximum value, answering every toss-up correctly, wagering their entire total on the last question of the final edition and answering correctly, and solving the Headline Extra puzzle with no clues.