Raymond started playing golf at the age of nine at the local nine hole course in Banbridge and rapidly made a name for himself in Irish junior golf by winning all five Boys titles. Under the guidance of coach Don Patterson he went on to gain Senior international, Walker Cup and Eisenhower Trophy caps before turning professional after the 1993 match. Failure to achieve his card at that year's European Tour Qualifying School proved a blessing in disguise, for Raymond spent a thoroughly profitable 1994 season on the European Challenge Tour. By the time he had celebrated his 21st birthday in October he had clinched a European Tour place with wins in Italy and Norway, and seven other top ten finishes to head the Challenge Tour Ranking with over £43,000. The pace then slowed, partly because of inconsistent putting, and the best performance of a rookie year in which he gained a place in the top 100 was seventh place in the BMW International Open.