Factual error: When Costigan is riding the "T" (Boston subway), he is talking to Queenan on a cell phone. However, they are on the "Red" line, which is obvious because of the red walls in the tunnel. Cell phones don't work on the Red line because it is underground and there are no cell phone routers in those tunnels.
Factual error: When Queenan and Costigan are riding the Red Line, Queenan gets on at Park Street station. Costigan tells him, "Get off at the next stop, South Station." South Station is two stops away; the next stop after Park Street is Downtown Crossing. However, Queenan does get off at the next stop, and it is magically South Station.
Factual error: When Costello throws the cocaine powder and says "Want some coke? Don't stop till you're numb" the pupils in his eyes are constricted. Cocaine, being a stimulant, dilates your pupils. Constricted pupils occurs with opiates - narcotic analgesic.
Factual error: When Costigan takes the Dr. Smith-prescribed Oxycontin tablets, the tablets are incorrectly shown as large, white oblong pills with the prescription bottle just labeled 'Oxycontin'. In reality oxycontin tablets are small, round, various colored pills (dependent on mg dose) with the dosage number (in mg) imprinted on one side of the tablet as 10, 15, 20, 30, 40, 60, 80, and 160 (I believe 160 mg tabs are discontinued) and the opposite side imprinted as OC or OP. Also, the dose (in mg) would have been printed on the front bottle label.