Raymond began his coaching career in 1949 as the head football and assistant boys' basketball coach at
University High School in
Ann Arbor, Michigan. He succeeded another former Michigan football player,
Henry Fonde. His football compiled identical 6–2 records in his two seasons as head coach and won a conference title in 1949. In 1951, Raymond became an assistant at the
University of Maine. He moved to Delaware in 1954 as a backfield coach under
David M. Nelson, who had also played at Michigan. When Nelson stood down in 1966 to focus on his duties as athletic director, Raymond succeeded Nelson as head football coach. He retired after 36 seasons with a 300–119–3 record, three national titles (1971, 1972, 1979), 14
Lambert Cup trophies, 23 post-season bids and four consecutive victories in the
Boardwalk Bowl. After classifications were formed in the early 1970s, Delaware was a Division II program until elevating to Division I-AA in 1981. At the time of his retirement, more than half of Blue Hens' all-time victories in the 110-year history of their program had been tallied under Raymond. On March 5, 2002,
K. C. Keeler, former Blue Hens linebacker and head football coach at
Rowan University, succeeded Raymond at Delaware.
Use of "Delaware Wing T" offense A formation similar to the Flexbone, though much older, is known as the "Delaware Wing-T" was created by longtime
University of Delaware coach and NCAA Rules Committee chairman
David M. Nelson, and perfected by his successor Tubby Raymond. It has become a very popular offense with high schools and small colleges. It was designed at the time to be a mix between the single wing and T-formation. It took the motion and run-strength of the single wing, and the QB-under-center from the T. In this variation, there is only one wing back, with the other back lined up next to the fullback on the opposite side from the wing back. However, the Wing Back may also line up diagonally from the Tight End. He may be used as an extra blocker or a receiver. He may come in motion for running plays.
300th win Going into the 2001 season, Raymond needed just four wins to reach the 300 mark. At the first game of the season, a banner hung above the stadium listing the numbers 297, 298, 299 and 300. As each win was accomplished, the respective number was crossed off. Raymond's 300th win came during the last home game of the season on November 10 with a 10–6 victory against the
Richmond Spiders. As the clock wound down in the game, the crowd began chanting "Tubby, Tubby". Raymond made a short, humble speech and was carried off the field by his team as a construction worker climbed onto a cherry-picker to cross off the final number on the poster. The following is an excerpt from Raymond's speech to Delaware fans after his 300th victory: "I have to apologize for paraphrasing, but I feel a little bit like
Lou Gehrig. I'm the luckiest man on the face of the earth. First, I'd like to thank the Delaware fans who have been here for so many years. I know there are things that happen that you don't like. There are things that happen that I don't like. But the thing that's there all the time is you. You're at every football game. You're excited about being here, and you truly made Delaware football something we can all be proud of. Thank you very much." Delaware lost its final game of the season on the road against
Villanova and, that winter, Raymond announced his retirement, ending his career at an even 300 wins. ==Awards and honors==