The subfossil remains of 14 cimicids (Hemiptera: Cimicidae) were recovered during archaeological investigations of the Paisley Five Mile Point Cave site (35LK3400), an exceptionally well-dated (n = 229 radiocarbon dates) late Pleistocene–early Holocene rock shelter site in south-central Oregon. Nine of the specimens have been assigned to three modern species of Nearctic Cimicidae—Cimex antennatus Usinger & Ueshima, Cimex latipennis Usinger & Ueshima, and Cimex pilosellus (Horváth)—whereas the remaining five individuals were too fragmentary to positively identify. The chronology of the insect assemblage puts one specimen at circa 5,100 calibrated years before present (cal. yr BP), and the remaining 13 range in age from 9,400 to almost 11,000 cal. yr BP. Although fossil and subfossil cimicid remains have been recovered at other archaeological sites, the fossil record for bed bugs is largely undocumented. The Paisley Caves specimens thus far represent the oldest remains of the genus in probable contact with humans on record.