Fleetwood was born in Southport, Merseyside. He 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, making his début at the 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.
In April 2017, Fleetwood 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.
|No.||Date||Tournament||Winning score||Margin of
|1||25 Aug 2013||Johnnie Walker Championship at Gleneagles||−18 (68-65-67-70=270)||Playoff||Stephen Gallacher, Ricardo González|
|2||22 Jan 2017||Abu Dhabi HSBC Golf Championship||−17 (67-67-70-67=271)||1 stroke||Dustin Johnson, Pablo Larrazábal|
European Tour playoff record (1–1)
|1||2013||Johnnie Walker Championship at Gleneagles||Stephen Gallacher, Ricardo González||Won with birdie on first extra hole|
|2||2017||Shenzhen International||Bernd Wiesberger||Lost to birdie on first extra hole|
|No.||Date||Tournament||Winning Score||Margin of
|1||11 Sep 2011||Kazakhstan Open||−15 (68-69-66-70=273)||2 strokes||Knut Børsheim|
|The Open Championship||CUT||CUT||CUT|
DNP = Did not play
CUT = missed the half-way cut
"T" indicates a tie for a place
Yellow background for top-10
Results not in chronological order prior to 2015.
DNP = Did not play
QF, R16, R32, R64 = Round in which player lost in match play
"T" = tied
Yellow background for top-10.
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