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Related to crossed path: cross-purposes, cross off, cross to carry
To match and execute two orders made to the same broker. Suppose a broker receives one order to buy 1,000 shares at $45 and another to sell 1,000 shares at $45. If he matches these two together, he is said to cross the orders. Crossing is subject to some regulation to prevent conflict of interest on the part of the broker.
To match, by a single broker or dealer, a buy order and a sell order. For example, a floor broker may have an order to buy 500 shares of IBM at $120 and another order to sell 500 shares of IBM at the same price. Subject to certain rules, the floor broker may cross the order by matching the sell and the buy orders. Crossing of stock is common in large blocks.