Rob Cragg began his intercollegiate diving career at the University of Pennsylvania in 1971 under diving coach Paul Flack. As a freshman, the varsity team went 7-6 overall and finished sixth in the Eastern Intercollegiate Swimming and Diving League championships. Cragg earned the Smith Award for the most points scored by a member of the Penn Swimming and Diving Team, winning 15 events between the one and three-meter diving boards throughout the season. His season high was against North Carolina State on December 9, 1971, where he scored 288.50 points on the one-meter board, beating two nationally-ranked divers from NC State.


As a sophomore in 1972-73, Cragg continued his high-flying escapades in swimming pools up and down the East Coast, soaring to a season-high score of 318.05 on the one-meter against Cornell on December 9, 1972. His three-meter high score of the season came against Navy on February 28, 1973 when he scored 299.00 points as Penn fell to the Midshipmen by three points. After finishing fifth at the Easterns, Cragg competed at the University of Tennessee in the NCAA Swimming and Diving Championships, placing 17th on the one-meter springboard. He was named to the All-Ivy team for his acrobatic efforts on the diving boards.


Cragg continued his reign as one of the premier divers on the East Coast as a junior in 1973-74. He won five one-meter competitions with his best performance of the season coming against Lehigh (315.60 points) on February 20, 1974. On the three-meter board, Cragg won four events throughout the season, scoring a season high 311.60 against Cornell on December 8, 1973. He was again named to the All-Ivy team and went on to compete in the NCAA Diving Championships where he was named to the All-American Swimming and Diving Team by finishing sixth on the one-meter springboard and ninth on the three-meter board.


In 1974-75, Cragg capped his highly successful intercollegiate career with All-Ivy honors for the third year. He was also named the 1975 Irwin Waldman Award winner as Penn's Most Inspirational Athlete. Cragg won both the one and three-meter diving competitions in 11 of the Quakers' 13 meets that season. His best performance on the three-meter board that campaign came against archrival Princeton, as Cragg scored a career-best 337.50 to finish first. Cragg set a career mark on the one-meter board with a score of 344.90 points on February 5, 1975 against Rutgers.


Upon completion of the dual-meet season, Cragg continued his senior year successes by winning the Eastern Intercollegiate Swimming and Diving Championship on the one-meter springboard and finishing second on the three-meter board. He then went on to Cleveland State University to compete in the NCAA Diving Championships, finishing fourth on the one-meter board and seventh on the three-meter board. This performance earned a repeat All-American appointment and scored all of Penn's points for this meet. How impressive was this performance? Cragg's cumulative points earned the Quakers' 17th place overall in the team competition. Penn was the highest Ivy League finisher at the NCAA Championship that year, and to this day, ranks as the best team performance Penn has ever achieved in this National Championship. Cragg also went on that year to finish third on the one-meter springboard and fifth on three-meter in the U.S. Diving National Championships.

After college, Cragg continued with his diving. In 1976, he earned a spot on the United States Olympic Team. In Montreal, Canada, Cragg finished in fifth place in the three-meter springboard diving event. He was also a member of the United States National Diving Team until his retirement from the sport in 1980. He continued his love for the sport by serving as the coach of the University of Pennsylvania diving team from 1987 through 1991.


"I always wanted Rob to come back and coach here. He is a Penn graduate and there is nothing like that. He has a great ability to articulate what he wants. Rob is very verbal and he always gets the best out of his divers . . . Overall, he presents the best image of Penn." - former Penn swimming coach Kathy Lawlor