As a flying three year old, Chester won seven of his ten starts, setting three race records. He placed short-head second in the AJC Derby. Two starts after the AJC Derby, he started in the VRC Derby, he won, and claimed a track record - 2:43 - a record that held itself until 1897 by Amberite. His next race, just a tender three days after his Derby triumph, was the gruelling two-mile (3200m) Melbourne Cup over a slippery, muddy track. Chester held on to beat the lightly weighted Savanaka by a half-head in the record time of 3:33-1/2.
He took a long and deserving spell after his spring campaign, and didn't return to racing until the April 1878. During his return, he won the AJC Autumn Stakes and two days later took second to Savanaka in the two-mile Sydney Cup, giving Savanaka twelve pounds. He won the AJC Cumberland Stakes over two miles, the next day winning the three-mile AJC Plate.
Lame for the majority of his next season, Chester ran twice. He won the AJC Spring Stakes over 12 furlongs, and came third in the AJC Craven Plate. He didn't show himself up until a year later, he ventured out for the VRC Melbourne Stakes, which he won, despite being lame. He was entered in the Melbourne Cup two days later, assigned with top weight of 9st.-6lb., but sore and out of condition for the two-miler, he placed sixth, with yet another Yattendon son, Grand Fleur, taking the money.
Chester led the sire's list in Australia in 1887-88, 1889-90, 1891-92 and 1892-93, the latter two posthumous placings since Chester died on the 21st of November, 1888, aged seventeen from rupturing his bowels.