Longboat was a "lengthy, attractive"[2] bay horse with no white markings bred by his owner Richard Dunbavin "Dick" Hollingsworth at his Arches Hall Stud in Hertfordshire.
On his final appearance of the year he finished second to the gelding Bedtime (also trained by Hern) in the Group Three Cumberland Lodge Stakes at Ascot Racecourse.
Later that month he was brought back in distance for the Yorkshire Cup, where he appeared unsuited by the soft ground and finished fourth behind Ilium, Old Country and Centroline.
[2] The soft ground which prevailed in the early part of 1986 was thought unsuitable for Longboat, and he missed intended runs in the Sagaro Stakes and the Yorkshire Cup.
Nine days after his run at Newbury, and racing on faster ground, he contested the Group Three Henry II Stakes over two miles at Sandown Park.
Racing on his favoured firm ground, he took the lead half a mile from the finish and was never challenged, winning by five lengths from Eastern Mystic, who beat Spicy Story by a head for second place.
Timeform were of the opinion that the field had been an unusually poor one, but praised the winner's "game and genuine" performance and admitted that he won in "tremendous style".
Carson sent him into the lead soon after the start and he was never in any danger of defeat, winning easily by ten lengths from Spicy Story, who was in turn well clear of the remainder of the field.
[8] In their book A Century of Champions, based on a modified version of the Timeform system, John Randall and Tony Morris rated Longboat as a "poor" winner of the Gold Cup.
[13] In January 1987, Longboat was sold for an undisclosed sum to Kerry Packer and Lloyd Williams and was exported to Australia with the Melbourne Cup at his objective.