Googlebot, Google's automated search agent was unable to differentiate between breaking news and a frequently viewed story when it picked up the old article on the Google News site.
Tribune said it identified problems with the Googlebot technology "months ago" and asked Google to stop using the search agent to crawl its newspaper sites.
The company claims that the six-year-old story titled "United Airlines Files for Bankruptcy" appeared on the Tribune-owned Sun Sentinel website under a tab called "Popular Stories Business: Most Viewed" during a period of low traffic early Sunday morning.
Despite Tribune's earlier request, it claims the Googlebot technology picked up the link and re-ran the story on the Google News site with dates changed to September 6 2008.
After the story spread swiftly across the web, United's parent company UAL reported a 70% drop in the price of its shares.
Google spokesman Gabriel Stricker disputed Tribune's claims and told the Los Angeles Times today that Tribune never asked Google to stop crawling their newspaper sites.
Traffic to the old story increased during the course of the day on September 7 with the bulk of it being referrals from Google. On Monday September 8, traffic increased even more after a summary of the Google News story was made available to subscribers of Bloomberg News.
United Airlines filed for bankruptcy in 2002 after the 9/11 attacks and a general economic slowdown triggered a sharp drop in revenue. The airline emerged from Chapter 11 protection in 2006 marking the largest and longest airline bankruptcy case in the history of the airline industry.
The current credit crunch coupled with soaring fuel prices now mean airlines across the globe are under constant speculation about their corporate finances, adding fuel to the frenzy when the 2002 United Airlines story ran this week.