1996
Darryll Holland remained in Hong Kong until June 1996 where he rode 32 winners, he finished 3rd in the Jockeys Championship which gave trainer Geoffrey Lane his best ever season.

Darryll returned to England and rode freelance before taking up an offer for a visiting Jockey to ride in Japan for 3 months. Whilst in Japan he rode Goldolphins biggest winner of the year "Annus Mirabilis".

In November Darryll returned to England to contest the 1st All Weather Championship which he went on to win.

1997
Darryll rode as a freelance Jockey from January 1997 to January 1998.
He rode 104 winners in the season.

1998
Darryll has had his best ever season in England, this year with a total so far of 127 winners, some of which are listed overleaf. He finished second in the Jockeys championship title.

He then rode a three-month contract for the Macau Jockey Club where he rode 10 winners.  He suffered a fall in Macau on December the 29th where he suffered a broken nose & cheekbone after a horse broke its leg in the race. The Doctor  signed him off until the 2nd of March 1999.

1999

Darryll was presented with an award at the 1999 Lesters award ceremony in London for the best flat race ride of 1998 on “Double Trigger” in the Doncaster Cup.
He made a comeback on the 15th of March after his fall. And rode freelance in England.

Darryll won the Group 3  Thresher Classic trial stakes at Sandown on “Fantastic Light” and Darryll ended the season in England on a high after winning the Group one Coral Eclispe at Sandown on “Compton Admiral”.

He then went to Singapore to ride for the Turf Club, he rode for 2 months and had 17 winners, out of 65 rides. Leaving in January as the leading visiting jockey.

2000

Darryll started riding on the all weather race courses in the UK to prepare for the flat season, then he got invited back to Singapore to ride in the International Singapore Airlines International Cup in March.

Darryll then got invited to ride in the Dubai World Cup.  Darryll won the John Porter Group 3 at Haydock on “yvannas pace”.  Darryll then went on to win the Singapore Derby Group 1 on the Godolphin trained “All the way”.

Darryll then won the Leicester Mercury stakes & the Tiomen Island Stakes both listed
races on “Murghem”, which he later rode in the Canadian Woodbine Meeting.  Then came back to the UK to win the Group 2 Geoffrey Freer Stakes also on “Murghem”.

Darryll continued to ride freelance, then won the Group 2 Sun Chariot Stakes at Newmarket on the Geoffrey Wragg trained “Danceabout”.

Darryll went on to ride many more winners and finished the season with a winner for Geoffrey Wragg in France, Darryll is currently riding in Singapore for the winter months.  He started his racing stint in singapore on the 2nd of December with an outstanding 4 winners, 2 seconds & 1 third out of 7 rides.

Darryll then went on the next weekend to ride another 4 winners in the same meeting, and was then invited to ride in the International races in Hong Kong riding the Singapore trained “Superb Effect”, the English trained “Murghem” and the German trained “Elle Danzig”