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Apple's stock closed 0.1 percent lower Monday, hitting a benchmark it hasn't in nearly two decades.
By ending the trading session lower, the tech giant extended its losing streak to eight days. The last time Apple fell eight consecutive trading sessions was July 1998.
Apple's stock, once considered a darling among Wall Street investors and analysts, has been under pressure recently.
The company reported its first-ever quarterly decline in iPhone sales last week, as well as its first year-over-year quarterly sales drop since 2003.
Over the past year, the stock has fallen more than 25 percent, and has shed nearly 12 percent in 2016.
AAPL in past 12 months