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Underwood set up UPH, a management and teamwork training company, with John Peters and Martyn Helliwell on 20 May 1999. Two years later, he appeared on Lily Savage's Blankety Blank.

Underwood took a ground-instruction job in 1995 at RAF Cranwell, becoming a flight lieutenant, while playing for Leicester. He became station flight safety officer, then joined No. 55 Squadron RAF (navigator training, now referred to as a weapon systems officer) on the twin-engined Dominie (British Aerospace 125), and continued in the RAF until 1999, although he could have stayed until 2001.

Underwood's long-lasting relationship with the RAF was put under strain when his wife was unfairly dismissed from the RAF for being pregnant, for which she received £13,000 in a compensation claim in 1995.

Underwood was capable of playing on either right or left wing depending on who was selected on the opposite side. More usually seen on the left wearing shirt number 11, in 1988 he switched to the right (and shirt number 14) to accommodate Chris Oti: in 1990 on the right opposite Mark Bailey, but on the left when partnering Simon Halliday, continuing on the left in 1991 opposite Nigel Heslop: in the 1991 World Cup he played on the right in partnership with Oti early on, then on the left in partnership with Heslop until the quarter-final and Halliday for the final two rounds, an arrangement that persisted throughout the 1992 Five Nations championship – which was initially billed as his final season before retirement, Underwood scoring tries in each of the first three matches of the championship, and coming close to scoring against Wales. However, Underwood changed his mind and opted to carry on, initially for the next match against South Africa (their first match since their readmission to international sport), and eventually for several more years – playing mostly now on the left, to accommodate his younger brother, Tony, on the right wing. They were the first brothers to represent England at the same time since 1937: and, in the 1993 match against Scotland, the first pair of brothers to score tries in the same match for England. He has been described as one of the greatest wingers to ever play the game.

Having first played as a youngster at Middlesbrough Rugby Club (with Rob Andrew and Bernie Coyne), Underwood went on to become one of the greatest wings in rugby union. Underwood is the leading try scorer for England in international matches. He first played for England in February 1984 against Ireland at Twickenham. He won 85 England and 6 Lions caps between 1984 and 1996 (then an English record, later surpassed by Jason Leonard – it remained the highest total for an English back, though that has since been overtaken by Jonny Wilkinson), scoring a record 49 tries for England, and 1 for the British Lions, making him one of the leading try scorers of all time. He played for England in the Rugby World Cups of 1987, 1991 and 1995.

Underwood's early life was spent in Malaysia. His family moved to Yorkshire in 1976, but his father was posted to Singapore and did not rejoin the family for another three years.

Rory Underwood, MBE, DL (born 19 June 1963) is an English former rugby union player, he is England's record international try scorer with 49 tries in 85 internationals between 1984 and 1996. Underwood's principal position was wing and he played 236 games for Leicester Tigers between 1983 and 1997, he also played for Middlesbrough, Bedford Blues and the Royal Air Force. Underwood toured with the British and Irish Lions in 1989 and 1993 playing in six tests and scoring one try. In 1992 Underwood played for England alongside his younger brother Tony Underwood, becoming the first brothers to play together for England since 1937.