Anyways, courtesy of the Wayback Machine, here's a pictorial look at OttawaSenators.com main page over the years (click on images for bigger size). Note: If you go to OttawaSenators.com on this site, you'll notice that quite a few of the pages still have workable links to other parts of the site at that time. You can spend hours in there, like that movie The Cube.
November 1996: Note the "Senators Moving To The Corel Centre" still under the Breaking News section. They moved to the "Palladium" in January of 96. Slow news year.
December 1997: The Sens have yet to put a player on their main page but they do manage to get the Damian Rhodes mask up, ostensibly because it says "The Net" and this whole internet thing was still in its honeymoon phase. "It's Time To Browse!".
February 1999: Here's a glimpse at a player profile page, Ottawa's own Jason York who, when asked what stick he uses, said "branches".
October 1999: The first fairly cool looking main page the Sens had. I remember this one well. Not sure who that player really is, but I used to think it was Radek Bonk.
December 2000: Back then it was big news that Daniel Alfredsson, Marian Hossa and Radek Bonk were opening up e-mail accounts, as noted on the front page here. Now it's Twitter. In 15 years? Time machine apps.
November 2001: Of the 9 names on the Best Coach In The NHL Poll, only 3 are head coaches today, soon to be 2 (guess who?).
November 2002: Sharp looking banner with Martin Havlat, Patrick Lalime, Wade Redden and the captain, but not the best slogan the Sens have gone with. "Be a Fan!".
March 2003: March 24 - Senators recall Brian Pothier from Binghamton.
October 2005: The main bit of news that day was the Sens lost their first game of the pre-season. Their record stood at 6-1-0. Those were the days. Dominik Hasek looked pretty good in a Sens uni.
March 2006: The Senators started to use splash pages around this time and they went with a great design here with the Big Z. This was when they were still using their original 2-D logo on the white jerseys and on merch. One day they will realize how good of a logo they actually had and resurrect it in some way. I'd give it 10-15 years.
That's about as far back into the future as we will venture today.
Except for this: Black Aces circa 2005. (It takes a bit to load. Just hit "Impatient" and it will load right away) Looks messy because it was messy.