Flying High: Rory Underwood on Life in the RAF and Rugby
Recently I had the privilege of chatting to Rory Underwood MBE. For most people they recall him as a professional rugby player with blistering pace on the field, his record-breaking 49 tries for England, together with his appearances with the British and Irish Lions. But spending time speaking with him, and you quickly realise there’s another story, that is lesser known, one of discipline, precision, and service in the Royal Air Force that ran parallel to his glittering sporting career.
I certainly felt that his life in the RAF was not a sideline to rugby, but every bit as central to him and who he is.
Balancing Act: The Early Years
“I’d always wanted to fly,” Rory says simply. Born in Middlesbrough in 1963, he set his sights on the skies long before rugby became a serious proposition. After studying at Barnard Castle School, County Durham, where his rugby career was beginning to gather pace, he joined the RAF in 1983. “Joining the RAF was the career I had in my sights when I was growing up,” he reflects. Flying fast jets was his ambition.
At the time, rugby union was still an amateur game. He would often tell people that the RAF was his job and his hobby was playing rugby albeit at a high level. It wasn’t a paid job, so training was fitted around work commitments then playing games on Saturday, but the rest of the time it was work and both careers ran in parallel. While breaking into the England squad in 1984 and establishing himself as one of the most exciting wingers in world rugby, Rory was also learning to fly some of the RAF’s most demanding aircraft.
Life as an RAF Pilot
His Royal Air Force career saw him commissioned as a flying officer, eventually rising to the rank of Flight Lieutenant. Rory flew the Tornado GR1, the venerable Canberra, and later the Hawk. He served with No. 360 Squadron and No. 100 Squadron, based at RAF Wyton.
“With the right mindset and discipline, it’s possible to excel at several things at once—my job was flying jets for the RAF, my hobby was playing rugby for England and Leicester Tigers,” Rory explains. While it might sound almost casual, there’s no mistaking the work ethic that underpinned his success in both arenas.
Upon chatting about the aircraft that enjoyed flying the most he speaks with particular fondness of the BAE Systems Hawk. “The Hawk was just a joy to fly,” he recalls, his face lighting up at the memory. “It was nimble, responsive, and had this beautiful balance between performance and control. As a pilot, you felt part of the aircraft, rather than just flying it. There’s something very special about that.”
As an instructor, Rory spent many hours helping to mould the next generation of RAF pilots. “I was constantly learning from each discipline to help me hone my skills,” he explains. The lessons he picked up in the air made him a better rugby player. The lessons from the rugby pitch made him a better pilot and leader.
But of all the aircraft he flew, the English Electric Canberra holds a unique place in his story. Specifically, WD955—a machine with its own distinguished history.
Canberra WD955: A Piece of Aviation Heritage
“Flying WD955 was like stepping back into another era,” Rory says with quiet respect. The Canberra was the RAF’s first jet-powered bomber, entering service in the early 1950s. It was revolutionary in its day—fast, capable of high-altitude flight, and with exceptional endurance. WD955 was among the early production models, having first flown in 1954.
This particular aircraft saw service as part of No. 360 Squadron in its later years. By the time Rory flew her, WD955 had been converted for electronic countermeasure (ECM) duties—a role that involved simulating enemy radar threats during exercises and providing valuable training for aircrews. “She was an old lady by then,” Rory says, “but a magnificent one.”
WD955 had the distinction of being one of the longest-serving Canberra airframes in RAF history, clocking up decades of operational flying. For Rory, flying her was both a privilege and a challenge. “You could feel the history in every rivet and panel,” he recalls. “It was a very different experience from the Hawk or Tornado—no fly-by-wire, no modern avionics. You had to fly her properly. She kept you honest as a pilot.”
Flying a machine with that kind of heritage also brought a sense of responsibility. “You realise you’re just one in a long line of pilots who’ve sat in that seat,” Rory says. “It’s humbling.”
Rugby at the Highest Level
At the same time as flying Hawks and Canberra’s, Rory was amassing an international rugby career that remains the benchmark for English wingers. Winning his first cap in 1984 against Ireland, he would go on to represent his country 85 times, scoring 49 tries a record that still stands today I believe.
During the week, he might be flying sorties or instructing new pilots. At weekends, he would line up for England or his club, Leicester Tigers. “It was a juggling act,” he admits, “but I thrived on it. I liked the challenge, the variety.”
His military career meant he was not always able to train full-time with his club or country. In an era before rugby union turned professional, Rory’s life was a delicate balancing act. “There were times I’d be flying on the Friday and playing international rugby on the Saturday. That was normal for me.”
Lessons from the RAF
When asked about the influence the RAF had on his rugby, Rory doesn’t hesitate. “The discipline, the preparation, the debriefing culture, those are all things I brought from the RAF to rugby. After a flight, he would spend hours going over every detail, what went right, what didn’t. That brought a mentality into how he approached games.”
It also helped him deal with pressure. “When you’re flying, mistakes can be fatal. That gives you a sense of perspective. You learn to stay calm, stay focused.”
Life After Rugby and the RAF
Rory eventually left the RAF in 1999, having served 18 years. By then, his rugby playing days were over, but he was already thinking about how to apply his experiences to the world beyond sport and the military.
Today, he runs a successful strategy consultancy, Wingman Ltd drawing directly from those dual careers. “People often separate sport and business, or military and sport, but the principles are the same,” he says. “Teamwork, communication, leadership—they’re universal.”
In 1992, Rory was awarded the MBE for services to rugby, but anyone who’s spoken with him knows it represents a lifetime of service in many arenas. As one bio neatly summarises, “Throughout his record-breaking rugby career, Rory amassed 18 years flying as a pilot in the Royal Air Force.”
The Legacy of a Dual Career
Speaking with Rory Underwood, you quickly understand that his story isn’t just about rugby tries or flying jets—it’s about a relentless pursuit of excellence, wherever he found himself. “I’ve always believed in pushing myself,” he says. “If you’re going to do something, do it properly.”
His RAF career, though less known to the public, was every bit as significant as his sporting achievements. It shaped him, grounded him, and ultimately helped make him one of the most respected figures in British sport.
For anyone looking to follow a similar path—whether in service to country or chasing sporting dreams—Rory Underwood remains an exemplar of what is possible with dedication, discipline, and a refusal to settle for anything less than your best.
