Derrick Cheshire

Derrick Cheshire

1903-1973

Article by Alan Trout

Derrick James Cheshire rode during the 1920s, recording three wins on the Flat and six over jumps. Born in 1903, he served his apprenticeship with James Hackett and had his first ride at Epsom on April 29, 1921, when partnering Tingle, who finished unplaced in the Great Surrey Handicap, won by Steve Donoghue on Pretty Girl. It was not until August 6 that he had his first winner when bringing home Mint Leaf to win the Apprentice Plate at Brighton by two lengths. 

Although Derrick rode occasionally on the Flat thereafter, it was under National Hunt rules that he next struck, when Harrismith, owned and trained by leading amateur rider Adam Scott, won the Kelso Handicap Hurdle at that Scottish venue on April 24, 1922. The seven-year-old followed this with a four-length victory in the Rudyard Handicap Hurdle at Uttoxeter on 9th May. Despite that promising start it was not until the corresponding race in 1927 that Derrick next visited the winner’s enclosure, when riding Irish Boy to score by a head. Three weeks later he rode Indiscretion to land the Green Selling Handicap Hurdle at Shirley Park. 

The next twelve months saw Derrick win twice under both codes. He had his first win on the Flat for six years when Rath Duth won the Piercefield Plate at Chepstow on July 8, 1927. Then, at Birmingham, he rode Mon to beat Repaid, the mount of ‘Brownie’ Carslake, by a head in the Aston Selling Plate. 

Another lengthy wait ensued before Dark took the Olton Handicap Hurdle at Shirley Park in April 1928, beating Notary, ridden by Billy Stott, then on his way to his first jockey’s championship title. The last of Derrick’s nine winners was a dead-heat at Cardiff on Whit Monday, May 28, 1928, in the Plymouth Handicap Hurdle The judge could not split William Bartlett on Rock Arrow and Derrick on Dark in a thrilling three-horse finish, with Billy Stott just a short-head behind them on Wild Duke. 

Derrick was the brother of jockey Frank Cheshire, who was killed at Sandown in 1921. Frank told Derrick before that fatal race that he thought his mount Cormac was a lovely horse and a splendid jumper, and that it was certain to win. At an inquest held at Esher the following Monday, Derrick, who had watched the race from the grandstand, said that he thought Frank's horse had taken off too soon. 

Derrick Cheshire did not renew his licence in 1929. He died in 1973. 

His winners were, in chronological order:

1. Mint Leaf, Brighton, August 6, 1921

2. Harrismith, Kelso, April 24, 1922

3. Harrismith, Uttoxeter, May 9, 1922

4. Irish Boy, Uttoxeter, May 10. 1927

5. Indiscretion, Shirley Park, May 30, 1927

6. Rath Duth, Chepstow, July 8, 1927

7. Mon, Birmingham, August 1, 1927

8. Dark, Shirley Park, April 30, 1928 

9. Dark, Cardiff, May 28, 1928 (dead-heat)