Oil prices tumbled below $14 per barrel Friday for the first time in five years as the energy markets continued to reel from worries about oversupply.

Friday's drop was tied mainly to selling pressure ahead of Monday's deadline to trade oil contracts for delivery in January.Light sweet crude oil for delivery in January settled at $13.91 per barrel, down 32 cents, at the New York Mercantile Exchange. Crude fell $1.16 per barrel during the week.

"This is a week where almost every day the market would make a brave attempt to rally but couldn't," said Andrew Lebow, senior broker at E.D.&F. Man International Futures Inc. "That's a sign of a bear market."

Crude oil prices have been hovering at five-year lows since the Organization of Petroleum Exporting Countries failed to curtail production at its November meeting.

There was little news to drive prices on Friday. There was some speculation that New York oil brokerage MG Corp. would have to sell its holdings because of financial troubles at its German parent company that led to a management shakeup.

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Prices frequently drop just ahead of the monthly contract expiration. Monday is the last day to trade January delivery contracts for crude on the Nymex. Investors who don't sell before then will face a tough time finding buyers or must take delivery of oil they hadn't planned on actually buying.

The February contract, which will represent the near-month delivery price on Tuesday, settled at $14.42 per barrel.

Unleaded gasoline for delivery next month settled at 40.19 cents a gallon, down 0.01 cent. Home heating oil for delivery in January settled at 44.07 cents, down 0.48 cent.

Natural gas prices were mixed, with contracts for delivery in January settling at $2.105 per 1,000 cubic feet, up 3 cents. More distant delivery months were lower.

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