June 1999: Ebay is down for 22 hours,

June 1999: Ebay is down for 22 hours, costs $2 million

“Technicians traced the main cause of the outage to a problem with the Sun Solaris operating system, which overwrote files and corrupted the Oracle database. The database, Version 7.3.2.2, recognized a data block in an incorrect format, and that caused the main hardware–a Sun E10000 server–to crash.”
http://www.robotwisdom.com/log1999m06b.html

“Shoddy planning played key role in eBay outages”
http://web.archive.org/web/20000226094617/http://www8.zdnet.com/pcweek/stories/news/0,4153,407390,00.html

via HN discussion about recent Amazon.com outage - I haven’t yet seen a postmortem of that.
http://news.ycombinator.com/item?id=5146882
http://www.internetnews.com/ec-news/article.php/137251