A former NCAA college basketball player, Obie has been involved with the CFL since 1963 in the roles of player, coach, general manager, scout, and several front-office positions. He has a wife, Judy; and three children: Tracy, Jodi, and Coy.
In 1974, O'Billovich launched his CFL coaching career with the Rough Riders, first as a guest coach, and then assistant coach.
O'Billovich was named head coach of the Toronto Argonauts in 1982, a position he held until 1989. During his tenure at Toronto, the Argonauts appeared in the Grey Cup three times (1982, 1983, 1987), winning the Cup in 1983. He was honoured as CFL Coach of the Year in 1982 and 1987.
Bob O'Billovich joined the B.C. Lions in midseason on September 14, 1990. The Lions had been off to a dismal 2-8 start that season; they finished the season with an improved 6-11 record. O'Billovich remained as head coach of the Lions through the end of the 1992 season, a year in which the Lions finished at 3-15.
In 1993, O'Billovich returned to the Argonauts as general manager. The Argos began that season poorly, and O'Billovich took over as head coach on September 10, 1993. He coached for the remainder of the 1993 season and for the entirety of the 1994 season. At the end of the 1994 season, O'Billovich relinquished the head coach position to concentrate on his general manager duties. The Argos again had a poor start for the 1995 season and O'Billovich took over as head coach for the final nine games; the team finished the season with a lackluster 4-14 record.
O'Billovich was director of player personnel with the B.C. Lions from 2003 to 2007. In December 2007, O'Billovich was hired as general manager by the Hamilton Tiger-Cats.