The Cup was to be a competition between recognized national automobile clubs initially representing France, Germany, Great Britain, Belgium, Austria, Switzerland, the United States and Italy. Any club wishing to take part in the race was required to deposit the sum of 3,000 francs with the A.C.F. before 1 January 1900. The actual race to be held sometime between 15 May and 15 August. The race distance would be not less than 550 nor more than 650 kilometers. The cost of race organization would be divided amongst each of the participating clubs.
The regulations covering the cars were family simple. Two side-by-side seats occupied at all times with driver and mechanic weighing no less than 60 kg. apiece and a minimum empty weight of 400 kg for the vehicle. Any means or propulsion was allowed though electric cars never took part in the race and steam entrants were never able to get beyond the French elimination trials of 1904. Each nation would be allowed to select a team of three cars with the drivers being members of the respective club and the cars themselves had to be made in their entirety in the country whose colors they wore. It was these last rules that would cause constant contention. France's automobile industry dwarfed the other countries when it came to mortorsport competition.
A recent accident at the Paris-Roubaix motor-tricycle race had raised anti-motoring fever such that it was not known until the last moment if a race would even be allowed by the authorities. It finally came but greatly effected the level of participation and in the end there were only seven entrants in the initial race with two not starting including the German Benz of Eugen Benz and the American Winton of Anthony L. Riker.
The Winton driven by Alexander Winton, who had previously boasted of its qualities was hopelessly underpowered compared to its competitors, with a one-cylinder 3.7-litre (226 cu in) engine producing 16 bhp (12 kW) located under its driver, it still featured tiller steering rather than a proper steering wheel. Jenatzy drove a Snoeck-Bolide, a French Bolide licensed and built by the Belgian Snoeck company.
The racers were sent off from the start line in Ville-d'Avray at 3:14 am with all five cars setting off together and as expected the three Panhards took the early lead. At Chartres de Knyff lost top gear and his top speed was limited to 30 mph though still 10 mph faster than the American Winton. Winton had been very outspoken prior to the event regarding the qualities of his car - sadly it was only talk. Jenatzy was involved in the slaughter of no less than six dogs before he finally retired at Moulins. The Winton retired soon after that and the race was between Charron and Girardot in the remaining Panhards. The race was won by Fernand Charron, whom the critics felt least deserving a seat prior to the race, driving a Panhard-Levassor at an average speed of 38.6 mph. He was followed by his teammate, Girardot who was the only other driver to finish.
The American periodical The Horseless Age wrote at the time "it is the impression (in the USA) that the race was very badly organized, that insufficient preparations had been made for it and that it must be looked upon as a failure". It should be noted however that the periodical was not a big proponent of motor racing. In a bid to address these concerns, the next two Gordon Bennett Cup races would be run in conjunction with one of the city-to-city event.
Australian, Selwyn Francis Edge entered a 920 c.i. (17 liter) two-ton monster which he was only able to test en route to the race as it had been finished only four days before the event. Edge remarked on the car that "it was though a powerful pump had been attached to a smaller car, ad had been blown out". Montague Napier served as his riding mechanic. During the trip to the race the British Dunlop tires failed miserably and Edge was forced to mount new French rubber. This led to the team's disqualification, since the rules stated that tires must originate in same country as the entry. Napier having traveled so far decided to enter the open race to Bordeaux instead but was forced to retire with clutch trouble.
The Automobilclub von Deutschland (AvD) planned to host an elimination trial between three Mercedes cars, a Benz and a Canello-Durkopp out of Bielefeld to determine their three entries. Following Mercedes victory in the Nice-Salon-Nice race they were automatically awarded two places by the AvD.
This left Benz and Canello-Durkopp to compete in the trials for the third entry. However, neither competitor showed up at the eliminating trial, and the Mercedes were withdrawn as both cars that had been built with the required all-German parts had been sold, and the manufacturer determined there was insufficient time to build any more cars.
The Cup would only have the three French cars as starters. Charron, last year's winner was the first car sent off but had to stop almost immediately with valve trouble allowing Levegh to pass his rival. Eventually Charron was forced to retire due to "tyre troubles" and the Cup match was left to Levegh and Girardot. At various sections of the course spare parts, fuel and lubricating oil were guarded by the various teams. Edge however was "serviced" by his cousin Cecil who could only provide champagne and gâteau d'éponge (sponge cake). Any replacements for his car would need to be purchased. Levegh was eliminated at Sainte Maure when he damaged his car on one of the notorious caniveaux (drainage ditch) that crossed the road and the Cup was won by Girardot at an average speed of 37 mph. By contrast the winner of the open race, Henri Fournier had averaged 53mph, and Girardot's time saw him placed tenth overall.
The race involved the Paris-Innsbruck section of the Paris-Vienna city-to-city race. Still there was a dearth of entries for the Cup with only 6 for the former as opposed to 213 for the latter. Still the French fielded a strong team time comprised from three different manufacturers with last years winner Girardot driving a Charron, Girardot et Voigt (C.G.V.), rising star Fournier driving a Mors, and De Knyff driving a Panhard. The British entries were comprised of the aforementioned Edge along two Wolseleys driven by Montague Grahame-White and Arthur Callan.
The competitors strongest test came just before the end when the cars had to cross the Murderous Arlberg pass described in The Automotor Journal in these forbidding tones:
This relatively light car was the sole survivor in its class able to reach Innsbruck and so claim the trophy. Its green color henceforth became known as "British Racing Green".
It took more than two decades before Great Britain was once again on the top rung of international motoring with the victory by Segrave in the French Grand Prix of 1923. Edge besides being the winning drive was Napier's sole agent and would later remark that his two largest contracts, one from America and one from France for napier cars were absolutely the direct result of winning the Gordon Bennett race. Annual output at the factory at Lambeth increased from 100 to 250 cars requiring a new factory being built in Acton.