The first private match, under the auspices of the club, seems to have come off, between two of the sailing boats, on April 20, 1776, but no mention is made of their names. Some of the expressions used in the newspapers about the different matches are very curious; in one paper it is called 'Fluviatic and Fresh Water Frolics,' and in another 'Thamesian Pleasantry,' and again, 'Water-racing Galloways,' but the best of the lot is in the 'Morning Post'[8] of 1782, where the race is described as 'a Fluviatic Cavalcade.'
Lines of Commodore Taylor's yacht, first 'Cumberland,' of Cumberland Fleet (Thames), 1780.
Winner of Gold Cup, 1780.
The yachts belonging to the Cumberland Fleet did not confine themselves to river sailing, for in one of the papers of 1777 it is stated that the 'Hawke' had been cruising about the Channel, and had been chased into Calais by an American privateer. The Duke of Cumberland gave a silver cup each year, of the value of twenty guineas; but in 1781, when the seventh became due, a silver-gilt cup of the value of fifty guineas was presented to the club by His Royal Highness. This was to be sailed for by the boats that had won the former prizes, and the advertisement goes on to say, 'The members of the Society do hereby, with the permission of His Royal Highness, challenge and invite all gentlemen, proprietors of pleasure sailing boats, within the British dominions, to join with them in the contention.'[9] The first attempt at this race on June 25 failed for want of wind, and the match had to be re-sailed on July 9, when the cup was won by the 'Cumberland,' belonging to Commodore Taylor. This race, the first open match ever sailed, seems to have caused a good deal of excitement, and the river and its banks were densely crowded. The papers of the day speak of the many thousands present, of all sorts, 'from the peerless "Perdita" to the Princess "Ran."'[10]
For some unexplained reason, 1782 was the last year that the Duke gave a cup to the 'Fleet.'[11] He certainly remained its patron up to his death in 1790, but he ceased to take any personal interest in the affairs of the club. This cup was won by the 'Caroline,'[12] belonging to Captain Coffin, and seems to have had a curious history, as in 1886 it was discovered in a pawnshop at San Francisco, and, it is said, was bought and raced for by some yacht club in America. On August 10, 1782, the first below-bridge match of the Cumberland Fleet took place. It was between the 'Caroline,' Captain Coffin, and the 'Eagle,' Captain Grubb, for a wager of 40l.: the course being from Cuckolds Point to the Lower Hope, and back again. The 'Caroline' won easily.
Lines of Commodore Taylor's yacht, second 'Cumberland,' launched February 14, 1790.
The years 1783 to 1785 have no matches recorded against the club. On August 21, 1784, the commodore's boat the 'Cumberland' went badly ashore on the rocks off Margate.[13] She must, however, have been afterwards saved, as she was commodore's boat at the match of 1786. A new era opened to the 'Cumberland Fleet' in the year 1786.[14] Jonathan Tyars became proprietor of Vauxhall Gardens, and to celebrate the jubilee of the Gardens (which had been open just fifty years), and also the new management, he gave an annual silver cup and cover, to be sailed for by the Cumberland Fleet, and a wherry to be rowed for by the watermen on the Thames.