Back when he was still doing stand-up, Bill Cosby had a joke about historical coin tosses:
Some of the ones he mentioned:
British vs. Americans 1774
British lose the toss and are forced to wear bright red coats and march out in the open in straight lines. The Americans get to hide in the trees wearing clothes to best conceal their appearance as they practice guerilla hit and run battle tactics.
Custer vs. Sitting Bull 1876
Custer loses the coin toss. His army waits at the bottom of a hill as all the Indians in North America come stampeding over them.
I'd like to add:
French Canadians vs. Americans 1813
Americans lose the coin toss, French Canadians get support of Native Mohawks and 1,630 French Canadians and Mohawks sucessfully stave off an invading force of 4,000 Americans attempting to invade Canada at the Battle of Chateuguay on October 25, 1813. Over 150 years later Mayonaisse companies are still rejoicing in the boon in sales this victory later yielded in the Montreal area alone, let alone the rest of Quebec.
Billy Goat vs. Chicago Cubs 1945
In their first World Series appearance since 1908 the Chicago Cubs forbid a wealthy fan from bringing his Billy Goat to game 1 of the 1945 World Series. The owner of said Billy Goat puts a curse on the Cubs saying that not only would they not win the 1945 World Series, they'd never play in a World Series again... So far the Cubs appear to still be the losers.
Boy Scouts vs. Girl Scouts
Boy Scouts lose the toss, Girl Scouts get to sell a variety of tasty cookies... The Boy Scouts sell overpriced "gourmet" popcorn
George H. W. Bush vs. US Congress 1991
Bush loses the coin toss and is forced to raise taxes breaking a campaign promise leading to his squandering of a 90% approval rating and losing his re-election bid to Bill Clinton.
George Hamilton vs. Robert Duvall 1990
Duvall loses the toss and is replaced in the third and final Godfather installment by the perpetually grinning and tanned George Hamilton. It could be argued that those who paid to see this film also lost as they were subjected to a sub-par excuse for a sequel in what had otherwise been a brilliant series of films.
Sean Young vs. Michelle Pfeiffer 1990
Young loses the coin toss (and arguably her mind) and instead of playing Catwoman in Batman Returns is forced to humiliate herself by showing up dressed as Catwoman in a helicopter to tell Tim Burton that she IS Catwoman. Her career is yet to recover from this lost coin toss.
Al Gore vs. Katherine Harris 2000
Gore loses the coin toss and instead of delivering State of the Union addresses to the American people for the next four years he instead finds himself delivering State of the Union addresses to his bathroom mirror every morning as he shaves.
Democrats vs. Republicans 2008
Republicans lose the coin toss and are forced to run a crotchety old out of touch senator (as opposed to any one of a number of younger, better-spoken, and more "in touch" other candidates) for president against a younger, more appealing and photogenic (albeit inexperienced) Democratic challenger.