In the Hambletonian/Diamond match, each side wagered 3,000 guineas, half to be forfeited if one withdrew. The match was run in 1799 and by then bookmakers offered odds on each horse too.

A match was staged at Newmarket, over their 4 mile straight Beacon course, on Monday 25 March 1799. The famous Beacon course starts 5 miles from Newmarket and continues in a straight line to the winning post which is a mile from Newmarket town centre. This match, still common even in the late 18th century, was between Durham landowner Sir Harry Vane-Tempest's Hambletonian (1792-1818)and the horse-breeder Joseph Cookson's Diamond (1792-1819).

The match, for 3,000 guineas a side, half of which was forfeit, saw the 5-4 on favourite Hambletonian, win by 'half a neck' in 7 ¼ minutes. Betting at the Coffee Houses in the morning favoured Hambletonian at 5/6, but on course during the race Evens was offered against each horse. http://www.greyhoundderby.com/St%20Leger%201795.html

The race attracted large crowds and ‘drew together the greatest concourse of people that ever was seen at Newmarket’, according to The Sporting Magazine. Reporters went on to write that during the race both Diamond and Hambletonian had been ‘much cut with the whip’ and 'severely goaded with the spur’, Hambletonian, ridden by the jockey Francis Buckle, ‘shockingly’ so. He would win by a dramatic last-minute effort. nationaltrustcollections