[4] As a colt foal, Lord Windermere was sent to the Tattersalls Ireland in November 2006 and was bought for €30,000 by the County Kildare-based Kennycourt Stud.
[5] As a three-year-old gelding, Lord Windermere was offered for sale at Tattersalls Ireland in June and at Doncaster in August, but failed to find a buyer.
Lord Windermere returned to winning form at Naas in March, beating the four-year-old Ballynacree by three lengths over two miles.
[10] On his last appearance of the season, the gelding made little impact in a Grade II event over two and a half miles at Fairyhouse in April, finishing eighth behind the Jessica Harrington-trained Jenari.
He then finished second to Mikael d'Haguenet at Punchestown on 9 December and then won his first chase three weeks later at Leopardstown, beating the Willie Mullins-trained Marasonnien by two lengths.
At the Cheltenham Festival on 13 March, Lord Windermere started at odds of 8/1 for the Grade I RSA Chase over three miles in which he was ridden for the first time by Davy Russell.
I fancied him like mad – I thought he'd love the ground here[7] Lord Windermere began his third season in the Hennessy Gold Cup at Newbury Racecourse in England in which he was assigned a weight of 162 pounds.
On 14 March, Lord Windermere started a 20/1 outsider for the 2014 Cheltenham Gold Cup in a field which included Bobs Worth, Triolo d'Alene and Last Instalment.
In a finish described as "dramatic" and "controversial",[14] Lord Windermere prevailed by a short head from On His Own, with The Giant Bolster three quarters of a length back in third.
[13] On his first appearance of the new season, Lord Windermere was brought back in distance for the John Durkan Memorial Punchestown Chase over two and a half miles on 7 December.
In the Hennessy Gold Cup in February, he took the lead approaching the second last but was overtaken at the final obstacle and finished third behind Carlingford Lough and Foxrock.
Robbie McNamara was booked to ride the horse in the Grand National but after being injured in a fall at Wexford Racecourse he was replaced by Brian O'Connell.
[18] In retirement, Lord Windermere became a living legend at The National Stud in Newmarket, where he shares a paddock with former sprinter The Tin Man.