Fleetwood had a distinguished amateur career with included wins in the 2009 Scottish Amateur Stroke Play Championship and the 2010 English Amateur, and runner-up finishes in the 2008 Amateur Championship, the 2010 New South Wales Amateur and the 2010 Spanish Amateur and the 2010 European Amateur. He represented Great Britain and Ireland in the Walker Cup in 2009. He also reached number 3 in The R&A's World Amateur Golf Ranking, and number 1 on the Scratch Players World Amateur Rankings. In July 2010 Fleetwood finished as runner-up to Daniel Gaunt in the English Challenge on Europe's second tier Challenge Tour. He won the English Amateur at the beginning of August and turned professional shortly afterwards.
Fleetwood made his professional début at the 2010 Czech Open on the European Tour, where he made the cut and finished tied for 67th. In September 2011 he claimed his first Challenge Tour win at the Kazakhstan Open, which secured his place on the European Tour for 2012.
Fleetwood had a mediocre start to his first season on the European Tour, but after finding some form in the autumn he managed to retain his playing rights with a top ten finish in the South African Open his last tournament of the season.
In August 2013, Fleetwood won his maiden title on the European Tour at the Johnnie Walker Championship at Gleneagles. He won in a three-man sudden death playoff, after a birdie on the first extra hole to see off Stephen Gallacher and Ricardo González.
On 22 May 2015, Fleetwood scored an albatross on the par-5 4th hole at the Wentworth Club during the second round of the BMW PGA Championship.
2017 was Fleetwood's most successful year to date. In January he won his second European Tour event, the Abu Dhabi HSBC Golf Championship, by one stroke over Dustin Johnson and Pablo Larrazábal after a final round 67. In March, Fleetwood was runner-up in the WGC-Mexico Championship, a shot behind Dustin Johnson while in April, he lost in a sudden-death playoff at the Shenzhen International to Bernd Wiesberger, at the first extra hole. Fleetwood had come from eight strokes behind on the final day with a stunning round of 63 to set the clubhouse lead. In the playoff, Fleetwood found the green in two, but Wiesberger from trouble fired an approach to within five feet and holed the birdie putt for the victory. In June, Fleetwood finished fourth in the U.S. Open, while in July, he won the Open de France, beating Peter Uihlein by a stroke, after a bogey-free final round 66. He moved from 99th in the World Rankings at the start of the year into the world top-20.
Fleetwood made a successful start to 2018, winning the Abu Dhabi HSBC Championship by two strokes from Ross Fisher. He had a final round of 65, with six birdies in the last nine holes.
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