July 1991: Banned for seven days for excessive use of the whip after hitting short-head winner Horizon 19 times in the final two furlongs of a race at Sandown.
November 1991: Crowned champion apprentice with a record 79 winners.
August 1992: Arrived at Haydock too late to ride the favourite in the opener, took a fall in a later race then received a four-day ban for interference, ruling him out of the Ebor meeting at York.
September 1993: Handed an eight-day ban by the Jockey Club disciplinary committee after a series of whip offences.
March 1995: Appointed stable jockey to Mark Johnston.
April 1995: Banned for six days for mistaking the finish on Lady Kuynder at Wolverhampton and easing off a circuit too early.
July 1995: Announced a split with Johnston to ride in Hong Kong.
December 1995: Banned for five meetings in Hong Kong for dropping his hands on a horse who was beaten by just a short head.
May 1996: The Royal Hong Kong Jockey Club terminated Holland's licence to ride in the colony, without giving a reason. The decision is upheld on appeal.
October 1997: Completed his first seasonal century of winners.
October 1998: Ruled out of the entire Cesarewitch meeting at Newmarket by a five-day ban for irresponsible riding at Pontefract.
May 1999: Handed a 15-day ban, with a further six suspended, by the Jockey Club disciplinary committee for interference offences under the "totting-up". Another offence soon follows to invoke the deferred penalty and Holland eventually spent 31 days on the sidelines.
July 1999: Gained his biggest victory to date on Compton Admiral in the CoralEclipse Stakes at Sandown.
August 1999: Missed the ride on Gaelic Storm at Jagersro in Sweden after a mix-up over the time of the race. Subsequently failed an alcohol test and is barred from taking his two other mounts on the card.