2001
Darryll Holland continued to ride in Singapore up until March 2001, then left as leading jockey and went onto Dubai to ride in the Dubai World Cup.
Darryll returned to the UK and started riding as a freelance jockey, riding for many different trainers, the bulk of his rides were for Mark Johnston and Geoffrey Wragg.
Darryll married on September the 16th 2001 to Jacqueline in Newmarket.
He ended the UK season with 105 winners.
2002
Darryll took a break in the winter and arrived in the UK at the end of February to start riding freelance again. Darryll won the Italian and German 2000 Guineas on Dupont, and went onto win the Group 1 July Cup on “Continent”.
He finished in joint third place in the jockeys championship with 112 winners.
Darryll rode in the UK up until the invitation race in Hong Kong in December, then took a break.
2003
Darryll started riding in the UK at the end of February and still a freelance jockey and won The Group 1 Coral Eclipse for the second time on “Falbrav”, then went onto win the Group 1 St James Palace Stakes on “Zafeen”, then the Group 1 Queen Elizabeth II Stakes on “Falbrav”, then the Group 1 Dewhurst Stakes on “Milk it Mick”, then the Group 1 Juddmonte International on “Falbrav”, then the Group 1 Gran Criterium on “Pearl of Love”.
Darryll had many more winners and also won the best Flat ride of the year at the Lesters ceremony for the second time, for his ride on “Just James” at Newmarket.
Darryll finished the flat Uk season in second place in the jockeys championship and left just before the end of the season to ride “Falbrav” in the Breeders Cup Turf in America, then he went onto ride in the Melbourne Cup in Australia.
Darryll was then offered a licence to ride in Singapore for a month and he rode 10 winners. Darryll then went straight to Maurititus for the Internationl races and
the retirement of Pat Eddery, where he was the joint winner.
2004
Darryll started the season in late Feb on the all weather courses.
In May he won the Italian Oaks
In June he won the Vodafone Coronation Cup at Epsom Group 1 on Warrsan &
Group 1 "Chorist" Pretty Polly Stakes at the Curraugh in Ireland
On the 11th of July Darryll had a bad fall at Bath and injured his back.
Rode in the Shergar Cup at Ascot
In August he had to have small operation on his back at the
Wellington Hospital St Johns Wood London.
Darryll still manged to end the season with 152 winners
In November he went to Japan for the international jockeys championships then
went straight on from there to Hong Kong to ride as a club jockey for 3 months.
2005
March started the season by being a guest on the Channel 4 Morning line then riding his first Winner of the season.
He went on to the Dubai racing festival for one week then onto the Melbourne Cup in October.
November saw Darryll at the Japan Cup for one week then the Mauritius jockeys international day.
Back in the UK He broke his ankle riding work for Vince Smith.
