Inspired by the map contests, Glen proposed the first timeline contest in December of 2006.

Glen choose the POD for the contest: November 2, 1948 - Thomas Dewey narrowly wins the US Presidential Election. The contestants were asked to have at least one event for every year from 1948 to 2007. Notably, the contestants were asked to complete their timelines in secret.

The contest was decided by the AH.com populace in a poll thread. The winner was Jasen777 for his timeline For Want of a Newsreel. The contest overall was somewhat of a disappointment, as there was only one other timeline. Its author was Alcuin who has since joined the Hall of Infamy.

The POD for the contest was chosen by Jasen777 as his prize for winning the first contest. It is: In 1505, Martin Luther doesn't become a monk and goes on to have an ordinary and historically unremarkable career as a lawyer.

Rules, such as the one event per year requirement, were significantly loosened. In addition, contestants made their timelines in public, being asked to make a weekly update in their thread in the pre-1900 forum section.

The contest was again decided by the AH.com populace in a poll thread. The winner was Jasen777 for his timeline A Dropped Pen, in a close victory over Dreadnought Jenkins's For Want of a shove.

In a risky departure, it was being organized by Jasen777 instead of Glen.

The POD for the contest was: the Battle of Boyacá is a victory for Royalist forces.

The contest might have been decided by the AH.com populace in a poll thread. The result was a tie between maverick's Araremos en el mar and Nicomacheus's Brothers in Arms.