After graduating from Duke in 1983, Engelland went on to play professionally for nine years. First in the Philippines, he became a naturalized Filipino citizen where he spent two seasons and was a member of the Philippine national basketball team supported by San Miguel Beermen that captured the 1985 Jones Cup Championship, then back in North America, playing for the Topeka Sizzlers of the Continental Basketball Association (CBA) and the Calgary 88's of the World Basketball League (WBL). . He was once known by Filipino fans in PBA as Chip "the Machine Gun" Engelland for his superb shooting skills. In 1993, Engelland started his coaching career, introducing his basketball camps Chip Shots with the aim of helping players of all ages improve their shooting skills; two years later he founded the In-Net Corporation, strengthening his reputation as a clinician and advisor. He got his first job in the National Basketball Association (NBA) in the 1999–2000 season, serving as a shooting consultant for the Detroit Pistons. Three years later, he signed with the Denver Nuggets as the director of player development, holding the position for two season. Since the 2005–06 season Engelland has been serving as an assistant coach for the San Antonio Spurs. Engelland has won three championship with the Spurs in 2005, 2007 and 2014.