1789: three-year-old season At the Newmarket Craven meeting of 1789, Skyscraper collected 240 guineas in forfeits and also won a five hundred guineas race for colts and fillies, beating Maid of all Work. At the Newmarket Second Spring meeting he won the Prince's Stakes (one hundred guineas each), beating
Earl Grosvenor's Brother to Skylark, Lord Clermont's Pipator, and six others. While at Epsom he also collected seventy guineas from the
Earl of Egremont's three-year-old filly
Tag, on whom Sam Chifney won that year's Oaks. At Newmarket on 1 October the horse collected a 250 guineas forfeit (for a 500 guineas match) from Magpie as well as sixty guineas from Lord Egremont's Calomel. The next day he won eight hundred guineas, beating Skylark, Competitor, and nine others. Also at Newmarket he gained another £50, beating eight including Egbert, and collected 110 guineas from Sister to Lethe and 130 guineas from Braggadocio.
1790: four-year-old season At the Newmarket first Spring meeting Skyscraper won the Jockey Stakes (100 guineas each), beating Skylark, Pipator, and Pickle. At the Newmarket second Spring meeting he took on Sir Charles Bunbury's Glaucus in a match for one thousand guineas and was beaten. On 1 October he won the Subscription (140 guineas) at Newmarket, beating Escape (1785), but in a match for seventy guineas at the same meeting he was defeated by Skylark. The next day in a sixty guineas purse he finished fourth, the winner being Seagull.
1791: five-year-old season Skyscraper again had his first outing at the Newmarket first Spring meeting, with mixed success. He won the 1500 guineas, beating fifteen other horses, but in a Sweepstakes was third and last, being beaten by Spear (1786) and Shovel (1785). At the second Spring meeting he collected a forfeit of 150 guineas (for a 300 guineas each sweepstakes) from four other horses, including the Prince of Wales's
Highflyer colt and a
Pot-8-os colt. However, in a field of six for a Sweepstakes of fifty guineas each at the same meeting, he was runner-up to the
Earl of Clermont's Tally-Ho.
1792: six-year-old season Skyscraper began the 1792 flat season with disappointments, but finished it strongly. In a handicap of fifty guineas each at the Newmarket Craven meeting, he finished second to his younger half-sister Thalia. At the first Spring meeting he took on Mr Bullock's Buzzard (1787) in a match for 200 guineas and was beaten, but at the meeting he went on to win the King's Plate, beating Coriander, Gustavus (1785) and Toby, the last another of his half-brothers by Highflyer. At Stockbridge he won the Prince of Wales's Plate, again meeting Thalia and beating her in both heats. At Winchester he won the King's Plate, twice beating Cropper. At Lewes he was runner-up for the King's Plate to the
Earl of Egremont's Precipitate (1787), and at Derby he walked over in a race for fifty guineas. At Newmarket on 1 October he won yet another King's Plate, beating Skylark, and the next day won a race for sixty guineas, beating Skylark again.
1793: seven-year-old season The horse won no races in 1793. At the Newmarket first Spring meeting he was runner-up for the King's Plate to Coriander, one of the horses he had beaten in the same race the year before. At the second Spring meeting he finished fifth and last in the Jockey Club Plate. He was then retired to stud. ==Sire==