In his first season he reached the last 32 in the Mercantile Credit Classic and was the youngest ever Scottish Professional champion.He also became the youngest player ever to qualify for the World Championship, a record he holds to this day. He lost 10–8 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 13–12 to defending champion Joe Johnson, and the semi-finals of the Mercantile Credit Classic. Hendry and Mike Hallett combined to win that year's World Doubles Championship. In 1987/88 Hendry won his first world ranking titles, the Grand Prix, beating Dennis Taylor 10–7 in the final, and the 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.
No ranking titles came his way the following season, although he did win the New Zealand Masters and also his first Masters at Wembley.
Hendry made a strong start to the 1999/2000 season by winning two of the first three tournaments, including the British Open, where he made the fifth 147 break of his career and the first maximum in a ranking final. However, he was surprisingly defeated in the first round of the 2000 World Championship by devutant Stuart Bingham. By Hendry's high standards the 2000/01 season was a disappointment, as he failed to win a ranking event for the first time since the 1988/1989 season and reached only one final. Still he won the European Open the next season and came close to an eighth World Championship. Having eliminated defending champion O'Sullivan in the semi-finals (17–13), he lost narrowly to Ebdon in the final (17–18). The Welsh Open in 2002/03 and British Open in 2003/04 came his way, with his victory in the2005 Malta Cup being his most recent ranking success. However, following O'Sullivan's decision to not enter the 2006 Malta Cup, Hendry was able to regain the world no. 1 position in 2005/06 due to consistency in reaching the latter stages of tournaments without, by his own admission, reproducing his form of old. He reached the final of the 2006 UK Championship in a tournament memorable for his quarter final against Ronnie O'Sullivan, in which O'Sullivan unexpectedly forfeited the match at 4–1 down following a strong start by Hendry. The Scot then came back from 7–5 behind in his semi-final to defeat then-World Champion Graeme Dott 9–7, but lost in the final, 6–10, to Peter Ebdon. Following a disappointing season in 2007/2008 Hendry unexpectedly reached his 12th semi-final at the World Championships, a new record surpassing Steve Davis' 11. In doing so aged 39 he became the oldest player to reach the semi-finals of the tournament since Terry Griffiths in 1992.
Hendry started season 2008/09 with two losses in his first matches. He was beaten 1–5 by Stephen Lee in the Northern Ireland Trophy and 4–5 by Ricky Walden in the Shanghai Masters. He had more success in the Grand Prix, however, winning his first-round match with David Gilbert 5–4, before succumbing to the eventual winner, John Higgins, 2–5 in the next round. However in the next ranking event, the Bahrain Championship, he reached the semi-final, but he lost 4–6 to Matthew Stevens. In the next 3 professional tournaments, the UK Championship, the Masters and the Welsh Open, Hendry lost in the first round to Stephen Lee, Neil Robertson and Martin Gould respectively. He found some form in China Open, beating Robert Milkins and Ricky Walden, but lost his quarter-final match to Peter Ebdon, the eventual winner of the tournament. At the World Championship Hendry beat good friend Mark Williams 10–7 in first round. This win guaranteed Hendry a place in top sixteen of the rankings for next season. He then went on to win 13–10 against Ding Junhui. In that match Hendry reached another milestone: a 1000th frame won at the Crucible (also, in that very frame Hendry scored 140 points). On 28 April, Hendry made a 147 maximum break against Shaun Murphy. He eventually lost the match 13–11 to Murphy the next day to go out of the championship.At the age of 40, he became the oldest player to make a maximum in a ranking tournament and only the second player (after O'Sullivan) to make more than one 147 at the Crucible. Hendry ended up at no. 10 of the world rankings, falling outside the top eight for the first time since the 1987/1988 season.
In the 2009/2010 season Hendry won his opening matches in every ranking tournament, however didn't manage to get to a quarter-final until the China Open, where he lost 4–5 to Mark Allen, despite at one time leading the match 4–2. In the Masters Hendry lost in the first round. In the first round of the World Championship, Hendry defeated Chinese Anda Zhang. Hendry was 7–9 down in the best-of-19 match, but managed to win 3 frames in a row for a 10–9 victory. At the press conference he confessed, that, had he lost the match, he would have seriously considered retirement.He lost in the second round 5–13 against Mark Selby. Apart from the Main Tour tournaments he won the seniors invitation tournament "Legends of Snooker" beating Ken Doherty 5–3 in the final. Another important event was the much publicised challenge match with Ding Junhui played in Beijing, which Hendry lost 6–13.
In the 2010/2011 season season Hendry could not maintain his unbeaten run in the first round of ranking events, as he lost it at the Shanghai Masters against Martin Gould by 2–5. At the World Open in Glasgow Hendry recorded 3–0 whitewashes against Bjorn Hanneveer and Mark Davis, before he was beaten 1–3 by rival Ronnie O'Sullivan. At the UK Championship in Telford Hendry was drawn against another old rival, Jimmy White. Despite struggling with his game throughout the match Hendry came through 9–8, rolling back the years by compiling a match-winning break in the deciding frame. In the second round Hendry was defeated 6–9 by Mark Williams.Afterwards Hendry expressed his frustration with his form and revealed that he has been suffering from "the yips" for the last ten years, leaving him unable to cue through the ball and causing him to miss the simplest of shots. Hendry next tournament was the Masters, where he lost 3–6 against reigning World Champion Neil Robertson. He made his 10th 147 break at the 2011 Welsh Open in the opening frame of the last 16 round vs Stephen Maguire, but later lost the game. At the 2011 China Open Hendry whitewashed Matthew Stevens 5–0 in the first round, before losing to Ding Junhui 2–5 in the second round.At the 2011 World Championship, he beat Joe Perry in the deciding frame of their first round tie before going out in the second round to Mark Selby 4–13.
Hendry began the 2011/2012 season at the first event of the Players Tour Championship, and lost 3–4 against Kyren Wilson.As a result of this he was ranked number 17 after the event, the first time out of the top 16 since the 1987/1988 season.However, he moved back into the top 16 after reaching the second round of the inaugural Australian Goldfields Open.
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