Highflyer was bred by Sir Charles Bunbury who had acquired his dam, Rachel (b f 1763 Blank), from Peregrine Bertie, the 3rd Duke of Ancaster. Rachel also produced Mark Anthony (b c 1767 Spectator) who sired the Derby winner Aimwell (b c 1782). The only sister to Highflyer is said to have died two hours after dislocating her hip while running at Nottingham in 1783. Rachel herself died in the spring of 1781.

Highflyer was named by his next owner, Frederick St John, 2nd Viscount Bolingbroke, at a dinner party given by Sir Charles, after the highflyer walnut trees growing in the paddock where he was foaled.

Although Highflyer remained the property of Lord Bolingbroke, after his first race he ran in the name of Mr Compton until his purchase by Richard Tattersall in the spring of 1779. Racing for three years, he was undefeated and never paid a forfeit, a fact which the General Stud Book felt obliged to report. Due to an error in an earlier racing calendar another Herod colt of the same age had been mistaken for Highflyer, which induced some old sportsmen to place wagers on the uncertainty.

Following his sale for £800 to Mr Tattersall, an astute businessman whose name is well known throughout the racehorse world as the founder of the auction firm, he ran several more times, recouping his purchase price before his retirement from the turf. He was easily the best horse of his day, winning over distances from two to above four miles and earning over 9,000 guineas during his short career.

His impeccable pedigree included two crosses of the Byerley Turk, whose male line he helped to perpetuate, two of the Godolphin Arabian, three of the Darley Arabian and two of the Curwen Bay Barb. As one of the four dominant sires in the latter half of the eighteenth century, along with Eclipse, King Herod and Matchem, Highflyer was thought to be well suited for crossing with Eclipse mares, although his best son, Sir Peter Teazle was devoid of Eclipse.

He went to stud at Ely, Cambridgeshire, along with Pumpkin (ch c 1769 Matchem) and Tandem (b c 1773 Syphon), commanding an ever increasing fee, said to have been as high as fifty-one guineas, as his offspring continued to prove themselves, earning about 1200 guineas per annum in his later years. His offspring included three Derby winners, Noble (b c 1783), Sir Peter Teazle (br c 1784) and Skyscraper (b c 1786), four St Leger winners, Cowslip (b f 1782), Omphale (b f 1781), Spadille (b c 1784) and Young Flora (b f 1785), along with the Oaks winner Volante (b f 1789).

His success enabled Mr Tattersall to build Highflyer Hall which was named in his honour. The hall can be seen in the above portrait by John Boultbee. Along with his hall Mr Tattersall established a fine broodmare band, and although he rarely raced any young stock himself he has the distinction of breeding the St Leger winner Cowslip (b f 1782 Highflyer) and the Oaks winner Yellow Filly (ch f 1783 Tandem).

Mr Tattersall also bred Sister to Cowslip (b f 1789 Highflyer), the dam of the St Leger winner Sancho, Deceit (ch f 1784 Tandem), the dam of the Oaks winner Parisot (br f 1793 Sir Peter Teazle), Maid of all Work (b f 1786 Highflyer), the dam of the Oaks winner Meteora (b f 1802 Meteor), and Highflyer Mare (b f 1785), the dam of the Derby winners Didelot (b c 1793 Trumpator) and Spread Eagle (b c 1800 Volunteer).

Highflyer was Champion Sire from 1785 to 1796, and again in 1798. He died at Highflyer Hall in October of 1793, and had inscribed on his gravestone: "Here lieth the perfect and beautiful symmetry of the much lamented Highflyer, by whom and his wonderful offspring the celebrated Tattersall acquired a noble fortune, but was not ashamed to acknowledge it." Richard Tattersall died in February of 1795.