Chicago made it three wins from his last four races in the Wimbledon Stayers Stakes over 687 metres at the South London track on Saturday.
Seamus Cahill’s son of Milldean Panther, a 4-7 chance, was soon clear and went on to beat Brinklydominic by three and a half lengths in a fast 41.76sec.
Ballygibbon King made it a short priced double in the top 480 metre contest when hitting the front off the third turn to see off King Danni by a length and a half in 28.70sec.
Cahill’s bid for a treble in the Maiden Stakes was denied by Liz McNair’s Eden The Kid.
The August 13 puppy caught Cahill’s long-time leader Elevenerife on the line to score by a neck in 28.96sec.
Tony Taylor’s Brinkley’s Miami was soon clear in the Sprint (273m) to record 16.11sec, while Con Te Partiro justified 1-3 favouritism in the Hurdles contest to hold off Affane Duke by a neck in 29.36sec.