The war of 1812, by the views of both Americans and Canadians, was arguably the most pointless, poorly-commanded war (by both sides) that occurred between us. The Americans say they won because us Canadians realized how incapable Britain was of defending us, and demanded our independence as to raise our own standing army. We Canadians say we won because the Americans were technically the aggressors in the war, and despite all their efforts, gained no ground.
To show just how much of a tie game the War of 1812 was, the Americans stormed York (modern day Toronto) and burned the Canadian parliament buildings to the ground. The new nerve centre of Canada was re-located to Ottawa, which, despite its strategic location, was an absolute rust-bucket slum of a city at the time. In response the British sent a division of the Peninsular Army, which razed and pillaged quite a lot of American territory, including Washington. Result: Tie Game
Earlier in the war, the aggresions started with the American General Hull, who is depicted in Canadian history books to be a completely incompetent, xenophobic moron of a general. Hull predicted the war as being "A mere matter of marching". It very well may have been that easy for Hull, if he hadn't told his troops to burn and pillage the first few cities who indifferently allowed the Americans entry. General Hull later surrendered at the siege of Detroit, when a vastly inferior force of Canadian militia and Native Americans set up shop outside of the walls, and scared him into giving up the fort without a pitched battle. Of course the events after this would not be kind to us Canadians, General Brock, the mastermind of the "Detroit Bluff", was shot leading a charge at the battle of Queenston heights, where the Canadian armies managed to only barely weather out the storm of the American assault. The Aboriginal Chief Tecumseh, who had assisted Brock in several battles earlier, found his Aboriginal coalition surrounded; abandoned by their allies, and severely out-gunned and out numbered, the Aboriginal Coalition was butchered by the advancing Americans. Result: Tie Game
All in all, the War of 1812 wasn't so much a "War" in the scope of the TW series, but merely a series of military fiascoes and mishaps.