In his first season, he reached the last 32 in the Classic and was the youngest ever Scottish Professional champion, winning the 1986 edition. He also became the youngest player ever to qualify for the World Championship, a record he held until 2012 when Luca Brecel qualified at the age of 17 years and one month. He lost 8–10 to Willie Thorne who then applauded him out of the arena. In the next season he retained the Scottish Professional Championship title and reached the quarter-finals of both the Grand Prix and World Championship, losing 12–13 to defending champion Joe Johnson, and the semi-finals of the Classic. Hendry and Mike Hallett combined to win that year's World Doubles Championship. In the 1987–88 season, Hendry won his first world ranking titles, the Grand Prix, beating Dennis Taylor 10–7 in the final, and the 1988 British Open. He also claimed three other tournament victories, retaining both the Scottish Professional Championship and the World Doubles Championship (with Hallett), and the Australian Masters. By the end of that season he was ranked world no. 4 and was voted the BBC Scotland Sports Personality of the Year.