I see in a rather odd article about coin-tossing the Telegraph UK mentions the ancient Roman past-time which they erroneously call Head or Ships but which was actually called Capita vel Navia, Heads or Ships because of Janus, the two headed god (yes, the one January is named after, the god of beginnings).

Janus was a very frequent image on coins throughout Roman history but the coin referred to by Macrobius was called the "As" or "Aes Grave". It was a bronze coin that featured Janus on one side and a ship's prow on another. These were typically minted around the Punic Wars (early 3rd century BC) and were replaced eventually by the silver denarius.

To read the complete article, see:Heads or Ships: Roman Coin Flipping(badlatin.wordpress.com/2009/12/31/heads-or-ships-roman-coin-flipping/)

One of the most significant coin tosses in the United State's history involved the naming of the city of Portland, Oregon in 1845. Asa Lovejoy and Francis Pettygrove, who owned the claim to the land that would later become Portland, each wanted to name their new town after their respective hometowns of Boston, Massachusetts and Portland, Maine. Pettygrove prevailed in the coin flip, and the town was named Portland.

In 1903, the Wright brothers flipped a coin to see which one of them would take to the air in the first ever powered flight. Wilbur won the toss but his attempt was only partially successful. Orville's later flight was considered the first example of powered flight.

To read the complete article, see:Coin tossing through the ages(www.telegraph.co.uk/science/science-news/6911921/
Coin-tossing-through-the-ages.html)