Fifteen Love, ridden by Steve Drowne, won the feature race on the fourth day at Glorious Goodwood on Friday.
The 5-1 shot, trained by Roger Charlton, broke from an outside draw and weaved through the field to win the £150,000 Totesport Mile by a head.
The 4-1 favourite Masaalek was second with Dubai Touch third.
The winner is a son of Point Given, hence the tennis name, and his win followed up Third Set's success in the Totesport International.
"I was concerned before the race that he may miss the break, but he broke well," said Charlton.
"Steve said he didn't have a hard race, and that the gaps weren't coming so he had to switch round.
"You don't often win two big handicaps in a season"
"It will be hard for him to win another handicap so we will have to try him in Listed or Group races now, and I'll have to talk to Prince Khalid to try to keep him in the UK as he will ultimately go to America."
"This horse travels and picks up for you and when the gaps come he goes for them," said Drowne.
"He's so tough, he's won a Britannia and he ran well at Sandown from a bad draw but he's popped out today and won.
"You don't often win two big handicaps in a season."
Goodwood Cup (2m)
1. Yeats (J Murtagh) 8-15 Fav
2. Tungsten Strike (D Holland) 33-1
3. Sagara (Ted Durcan) 33-1
8 ran
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