Overstock.com Announces Day Five Winner of 10th Anniversary 'Daily Dig' and 'Twitter Like it's 1999' Sweepstakes

Grand Prize Winner of 2010 Toyota Prius hybrid to be announced on October 12, 2009

• Press Release
• Source: Overstock.com, Inc.
• On 7:32 pm EDT, Tuesday October 6, 2009

SALT LAKE CITY, Oct. 6 /PRNewswire-FirstCall/ -- Overstock.com, Inc. (Nasdaq: OSTK - News) announced today that Cassandra Coleman of Detroit, Michigan is the day five winner of the 10th Anniversary "Daily Dig" sweepstakes. Cassandra won a residential room makeover worth $5,000. Also, Max Gibbons of Honolulu, Hawaii is the day five winner of the "Twitter Like it's 1999" online Twitter sweepstakes. Max received a Flip UltraHD Camcorder. To enter the sweepstakes, visit www.overstock.com

"This is all part of our celebration. We want to give those consumers who visit our site the chance to win some great prizes," said Overstock.com Chairman and CEO Patrick Byrne.

"Daily Dig" contestants still have the opportunity to win a $5,000 jewelry package, luxury watch, a $5,000 shopping spree on Overstock.com, a dream vacation package worth $5,000, and a Grand Prize of a 2010 Toyota Prius hybrid, to be announced on October 12.

The "Daily Dig" sweepstakes participants can visit www.overstock.com to find a link to the contest page where contestants are given one clue each day to the "Daily Dig." The daily clue will guide them to search and find a specific product on the Overstock.com site. That day's specific product page will feature a 10th Anniversary logo with a link to enter to win that day's prize. Also on the contest entry page, participants can share the contest with friends and family.

As part of the "Twitter Like it's 1999" sweepstakes participants will need to visit www.overstock.com/twitter1999 each day to see what prize is up for grabs, and how to enter. To enter participants will need to follow Overstock.com on twitter (@overstock), visit www.overstock.com/twitter1999 each day from October 1-10 to see that day's 1999 Twitter theme. Users are then asked to tweet what they were doing in 1999, according to that day's contest theme and being sure to include the contest link and the #In1999 hash tag.

About Overstock.com

Overstock.com, Inc. is an online retailer offering brand-name merchandise at discount prices. The company offers its customers an opportunity to shop for bargains conveniently, while offering its suppliers an alternative inventory distribution channel. Overstock.com, headquartered in Salt Lake City, is a publicly traded company listed on the NASDAQ Global Market System and can be found online at http://www.overstock.com. Overstock.com regularly posts information about the company and other related matters on its website under the heading "Investor Relations."

Overstock.com® is a registered trademark of Overstock.com, Inc. All other trademarks are the property of their respective owners.

This press release contains certain forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Such forward-looking statements include, but are not limited to, statements regarding the course and process of the Sweepstakes. Our Form 10-K/A for the year ended December 31, 2008, our subsequent quarterly reports on Form 10-Q, or any amendments thereto, and our other subsequent filings with the Securities and Exchange Commission identify important factors that could cause our actual results to differ materially from those contained in our projections, estimates or forward-looking statements.

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