1991
Darryll Holland was Champion Apprentice Jockey in England,
Setting a new post war record for the number of wins by an apprentice in one season.

In only his second full season, he finished 11th in the professional Jockeys league table.

As well as the 83 wins in England he won the Listed Platinum Stakes at Fairyhouse in Ireland and the Listed Premio Del Piazzale Stakes at San Siro in Italy on a horse called "Sure Sharp".

1992
The first half of the 1992 season in England saw Darryll go through a quiet period, with his main stable suffering from the virus, but the turning point came on September 11th when he won the Group 3 Abtrust Select Stakes at Goodwood on John Gosden's "Knifebox" at odds of 25/1.

He went on to win two further Group 3 races on this horse at Maisons Laffitte in France, and San Siro in Italy.
Since September 10th, Darryll rode a total of 37 winners in England, which was only matched by Pat Eddery, and was indeed four more than champion Jockey Michael Roberts. 

Notable victories included the Group 3 Rockfel Stakes at Newmarket on "Yawl", and the Doncaster November Handicap on "Turgenev" and the Premio Guido Berardelli Group 2 in Rome on "Wootton Rivers".

1993
Darryll's main stable Mr Barry Hills, again suffered from the virus throughout the year, but he finished 3rd in the English Derby Group 1 at Epsom on "Blues Traveller" at odds of 150/1,  and also won the Group 3 Premio Natale di Roma in Italy on "Prospective Ruler", and the Austrian Derby on "Zimzalabim".

1994
Darryll was invited to take part in the young Jockeys World Championship in Japan held at Nakayama Racecourse on March 5th & 6th which was limited to Jockeys under the age of 28 in 1994 and having under 10 years of riding experience. 

He won the Global Cup on "Trideed", worth (13,700,000 yen) and finished 3rd in the opening cup on "Morikaiso", worth (9,900,000 yen).  He finished 4th out of 12 jockeys in the championship overall.

In England in 1994 Darryll became freelance and lacked the support of a major stable.  However, despite no single trainer providing more than 7 winners for him, Darryll still maintained his position as 12th in the table at the time he left for Hong Kong on August 29th 1994.  He won the first two major handicaps of the season, winning the Lincoln Handicap at Doncaster on "Our Rita", and the Queens Prize Handicap at Kempton on "Jonsalan".

In June 1994 Darryll received the offer of a contract to be a retained Jockey for the Royal Hong Kong Jockey Club for the period Sep/Nov 1994.

He decided to accept and was the youngest Jockey to be granted such a licence.

From Sep/Nov he rode 11 winners and was the current Champion Jockey and was asked to extend his stay for a further 3 months until February 1995 where he rode a further 17 winners.

1995
While Darryll was in Hong Kong he secured a retainership in England to Mark Johnston as 1st Jockey to Kingsley House Stables.

Meanwhile due to his great success in Hong Kong he was offered a very lucrative contract to ride a further season in Hong Kong as a retained Jockey for the top trainer Geoffrey Lane.  Darryll accepted the Hong Kong offer and began his contract in Hong Kong in September.