The Jester came from last and 14 lengths from the lead in a rating 85 1200m race to win by a length and a-half.
He extended the great record at Cromwell meetings for his owner-trainers, the Dennis brothers, Ray, Tony, Martin and Joe, of Woodlands.
They had their first Cromwell win 49 years ago with The Missionary.
The Jester, a 7yr-old gelding by Faltaat from The Reason, traces to Eager Lady, a Man's Pal mare who left The Missionary and The Budget, the first winner for Tony and Ray Dennis in 1960.
"It could be the Central Otago air and the fact that we get a good track. Horses can come from anywhere on this track and that was proved by The Jester," Ray Dennis said when asked for a reason for their successes at Cromwell.
The Jester was an impressive winner at Cromwell at his first start in November, 2008.
"He was making a noise [breathing with difficulty] after his next start and we had him scoped and there was a problem," Dennis said.
"We had to send him to Massey University to put him on a treadmill to find out exactly. It was something to do with his voice box and he had an operation."
The Jester has now won seven races.
• Gerard Bell, who turns 75 today, began celebrating yesterday when his horse, Windwhistle, won the $25,000 Cromwell Cup at odds of 29-to-one.
Bell, from Geraldine and formerly Alexandra, has Windwhistle in the Washdyke stable of Mel Coles (76), who trains the 4yr-old with his son Warwick.
Joy Dennison, of Washdyke, is also in the ownership with Warwick and Gerard.
Windwhistle was having his first start beyond 1600m when he won the 2000m event yesterday at his 39th start. He has raced steadily since he was a 2yr-old and has now won nine races and $84,110 in stakes.
The son of Traditionally and Ultra Vires was a $1600 purchase as a yearling at the South Island sale.
Bell had won a race at Cromwell in the 1980s with Sherrol Lee, trained by Mike Skerrett.
• Chris Johnson was fined $300 for a dual riding engagement. He was ordered to ride Stradbroke City in race 4 where there was a dispute with the mount for Whaa.
