What would you consider the "biggest" match in Raw history? I don't mean the best in terms of match quality, just the biggest marquee match they've ever given away for free on TV on Raw.
I think some matches kind of lose their value without the perspective of the climate they took place in. For example, the Austin vs Big Show ("Paul Wight") match in 1999 just before WrestleMania was a HUGE match at the time as Show had just come over from WCW and it could have easily headlined a PPV, but it's probably not a match people think of anymore when talking about the biggest matches ever.
My pick would be Rock & Austin vs nWo (Hogan, Hall & Nash). The star power in that match is crazy. Literally the 3 biggest stars in the business of all-time in the same ring at once, along with two of the most influencial.