Vigilant surging toward the finish line at Cowes on August 4, 1894, in the lead during her private match with Prince of Wales' cutter Britannia. After her defeats by Britannia on the Clyde and at the Penzance Regatta, where the yachts raced in an annual fixture on the way from the Clyde to the Solent, there was tremendous interest in this match race, especially as it was a prelude in Cowes Week.

Englishmen hoped for a hard breeze with plenty of windward work, which would suit Britannia. By the time Vigilant reached the Solent she had been tuned up and had her sail area slightly reduced. Her owner contacted Ratsey & Lapthorn to obtain an English suit of sails to replace the ill-fitting ones she had carried on the Clyde. The firm felt that they could not supply them and instead Vigilant's big mainsail was sent by rail from Penzance to Southampton, together with some of her headsails, where it was practically rebuilt by Tilling & Son.

Both yachts were docked for bottom cleaning and were remeasured at Southampton the day before the race, when Vigilant's crew turned everything possible out of her, even food and drinking water. As a result ofthe measurement, Vigilant had to allow Britannia 2 minutes 4 seconds on the course. The prize was a £100 silver cup (cost) to be given by the owner of the losing yacht to the owner of the winner. They started over the Royal Yacht Squadron line, westward to round the East Lepe Buoy, then to the Warner light ship off the east end of the Isle of Wight, then back to Cowes, twice round - in all about 42 miles. Hundreds of steam and sailing yachts crowded Cowes Roads to see the start of this international contest. The westerly wind was fresh and they made the East Lepe mark in three tacks over the foul tide, the only windward work of the day, with Vigilant leading by 50 seconds in the jibe around the mark to sail eastward, and setting a large jib topsail (such a sail was afterwards called a "Yankee jib topsail" by English crews), compared to the British yacht's ordinary sized one. Vigilant continued to draw away and a spectator wrote: “As the yachts threaded the fleet anchored in Cowes Roads they were heartily cheered. The crews of HMS Dreadnought, the German corvette Stosch and the Osborne, royal yacht, being particularly demonstrative.'

Off Seaview the breeze freshened and at the Warner the Vigilant was 2 minutes 44 seconds ahead. They reached back through Spithead and into the Solent, rounded the East Lepe and again back to the Warner, the jib topsails being taken in as the breeze freshened. On the reach back to the finish at Cowes, the German Emperor cutter Meteor was pacing Vigilant, which was also followed by her owner's large steam yacht Atalanta. Vigilant won by 4 minutes 29 seconds, a few minutes after this photo was taken. She is travelling at her maximum speed, perhaps 12 knots, in the smooth waters and will get fresher puffs when she clears the high lands at East Cowes. She carries her jib-headed topsail, and the large light weather jib topsail is stowed on the bowsprit, ready to be re-set if necessary. Someone, probably the first mate, checks the lee rigging and all hands are low on the broad deck as Hank Haff drives his Yankee "sloop" to victory.