Raymond Berry enlisted as a private in the Maryland Army National Guard on May 17, 1957. He was assigned to Headquarters and Headquarters Battery, 684th Anti-Aircraft Artillery Battalion (90 mm Gun), located near Baltimore. He subsequently served in Headquarters and Headquarters Battery, 684th Missile Battalion (Nike); Headquarters and Headquarters Battery, 224th Field Artillery Group; Headquarters and Headquarters Battery, 691st Anti-Aircraft Artillery Group; and Company B, 16th Special Forces Group, all components of the Maryland Army National Guard. He was discharged from the Army in March 1963, at the end of his second enlistment, with the rank of Specialist Four.
In high school (Paris, TX High School) and college, Berry caught very few passes. He didn't start on his high-school team until he was a senior, even though his father was the coach. After high school Berry played one year of junior college football at Schreiner University (then Institute) in Kerville, TX during the 1950 campaign. He helped the Mountaineers finish its most successful season in 10 years with a record of 7-3. In three seasons at Southern Methodist University, Berry received only 33 passes total before being selected by the Colts in the 20th round of the 1954 NFL draft. Of course, during the early 1950s, colleges specialized in the running game. As Berry said, "I didn't catch many passes because not many were thrown".
Berry, however, became a permanent starter on the team by his second NFL season, and didn't miss a single game until his eighth year in the league. During his career, he led the NFL in receptions three times, and was renowned for his great hands and precise pass patterns. In his career he only dropped a total of two passes and fumbled only twice. He was selected to the Pro Bowl six times, from 1957–61 and in 1965. He also made the all-NFL team from 1958-1960. Berry was considered the very identity of the great Baltimore Colts' teams of the 1950s and 1960s (along with Johnny Unitas, Alan Ameche, Lenny Moore, John Mackey, Gino Marchetti, Art Donovan and Jim Parker). He was famous for his attention to detail and preparation. He and quarterback John Unitas regularly worked after practice and developed the timing and knowledge of each other's abilities that made each more effective.
One of Berry's most notable performances was in the 1958 NFL Championship Game, known as "The Greatest Game Ever Played," in which he caught a championship-record 12 passes for 178 yards and a touchdown. During the Baltimore Colts' final game-winning drive in overtime, Berry had two key receptions for 33 yards. He also caught three consecutive passes for 62 yards to set up the Colts tying field goal at the end of regulation.
Raymond Berry ended his NFL career in 1967 with an NFL record 631 receptions for 9,275 yards and 68 touchdowns (14.7 yards per catch). In 1973, Berry was voted into the Pro Football Hall of Fame in Canton, Ohio. In 1999, he was ranked No. 40 on The Sporting News' list of the 100 Greatest Football Players.
Berry joined the New England Patriots as receivers coach under Chuck Fairbanks in 1978. He stayed on with new coach Ron Erhardt until Erhardt and his entire staff were fired following a 2–14 1981 season. Berry left football and worked in the private sector[clarification needed] in Medfield, Massachusetts, until the Patriots fired Ron Meyer in the middle of the 1984 season and hired Berry to replace him. Under his leadership, the Patriots won four of their last eight games and finished the season with a 9–7 record. Berry's importance to the team was reflected less in his initial win-loss record than in the respect he immediately earned in the locker room - "Raymond Berry earned more respect in one day than Ron Meyer earned in three years", according to running back Tony Collins.
In the 1985 season, the team did even better, recording an 11–5 record and making the playoffs as a wildcard team. They went on to become the first team in NFL history ever to advance to the Super Bowl by winning three playoff games on the road, defeating the New York Jets, 26–14, the Los Angeles Raiders, 27–20, and the Miami Dolphins, 31–14. New England's win against Miami was particularly surprising[according to whom?] because the Patriots had not beaten the Dolphins at the Orange Bowl (Miami's then home stadium) since 1966, in Miami's first AFL season. The Patriots had lost to the Dolphins there 18 consecutive times, including a 30–27 loss in week 15 of the regular season. In addition, the Dolphins had recorded an AFC-best 12–4 record and had been the only team during the season to defeat the Chicago Bears, who had stormed to the top of the NFC with a 15–1 record and advanced to the Super Bowl by shutting out both their opponents in the playoffs.
But despite the Patriots' success in the playoffs, they proved unable to compete with the Bears in Super Bowl XX, losing 46–10 in what was at the time the most lopsided defeat in Super Bowl history. "We couldn't protect the quarterback, and that was my fault. I couldn't come up with a system to handle the Bears' pass rush", Berry acknowledged.
The following season, Berry's Patriots again recorded an 11–5 record and made the playoffs, but this time lost in the first round of the postseason. That would be the last time the Patriots would make the playoffs with Berry as their coach. They narrowly missed the playoffs with an 8–7 record in 1987 (during a strike-shortened season) and a 9–7 record in 1988. Then in Berry's last year as a coach, the Patriots finished the 1989 season 5–11. New Patriots team owner Victor Kiam demanded Berry relinquish control over personnel and reorganize his staff; Berry refused and was fired.
Berry's overall coaching record is 48–39 (.552) and 3–2 (.600) in the playoffs.
*Tied for 1st place in their division, but since there was no tie-breaking system in 1965, a game was played to determine who went to the conference championship. The Colts lost the divisional playoff game.