Although Scottish by birth and ancestry, he was raised in Yorkshire, England, where his father, James Montgomerie, was Managing Director of Fox's Biscuits.

Montgomerie became one of the first British golfers to go to a United States college, attending Houston Baptist University, where he played on the golf team and became its top player.

He quickly developed into one of Europe's top pros, winning his first event at the 1989 Portuguese Open TPC by 11 shots, and his second, beating a world class field, at the 1991 Scandinavian Masters at Royal Drottningholm Golf Club in Sweden.

[10] A runner-up finish at the 2008 French Open in June boosted him back up the rankings, but his good play was short-lived, and as a result Montgomerie failed to qualify for Nick Faldo's 2008 Ryder Cup team.

In March 2009, Montgomerie played in his milestone 500th European Tour event at the Open de Andalucia where he made the cut, but was not in contention during the weekend.

After nearly two years without a top-10 finish, Montgomerie posted a final round of 68 for a share of 7th place in the 2011 BMW PGA Championship at Wentworth.

However, in 2016 he narrowly missed out on making it three Senior PGA Championships in a row – finishing second and three shots behind winner Rocco Mediate.

[17] Montgomerie is generally considered to be one of the best golfers never to have won a major championship, after finishing in second place on five separate occasions.

At the 2006 U.S. Open, played on the West course of the Winged Foot Golf Club, Montgomerie had yet another chance to win his first major championship.

He stood in the middle of the 18th fairway in the final round having sunk a 50-foot birdie putt on the 17th green, which put him in the joint lead with Phil Mickelson.

While waiting in position on the 18th fairway for the group in front to finish, Montgomerie switched his club from a 6-iron to a 7-iron, assuming adrenaline would kick in.

He was also in contention with two rounds to play at Muirfield in 2002 and Royal Troon Golf Club in 2004, but failed to capitalise and finished midway down the field.

He halved the last hole with Scott Hoch to obtain the half-point that won Europe the cup in 1997, and sank the winning putt,[24] in what is considered to be his finest hour in the 2004 staging of the event.

Montgomerie was not part of Nick Faldo's 2008 Ryder Cup team, with the wildcards going to Paul Casey and Ian Poulter.

Montgomerie captained the Great Britain and Ireland team in the first four stagings of the Seve Trophy, losing in 2000 but winning in 2002, 2003, and 2005.

[27] In December 2010, he accepted the BBC Sports Personality Coach of the Year award as captain of the victorious Ryder Cup team.

She was a 17-year-old law student at Edinburgh University and a spectator at an amateur championship in Nairn, at which Montgomerie destroyed the field.

In 2006, the couple finally broke up, with Eimear suing for divorce on grounds of unreasonable behaviour due to his obsession with golf,[33] claiming it left her suffering from anxiety and depression.

[34] In 2006, the couple agreed to a clean break divorce settlement of £8 million, in return for Eimear giving up any claim on Colin's future earnings.

[40][41] On 8 July 2010, Montgomerie was granted a super injunction by Mr Justice Eady, which came to light when he attended a press conference at the 2010 PGA Championship in Wisconsin.

[44] *Langer and Montgomerie agreed to share the 2002 Volvo Masters Andalucía after failing light caused play to halt after two holes of a playoff.