On his next appearance in November 2005, he won the Hennessy Cognac Gold Cup under the biggest weights carried to victory in the race for twenty years.

Ridden for the first time by Mick Fitzgerald he took the lead three furlongs from the finish but was caught in the closing stages and beaten a neck by Chelsea Bridge.

He started a 50/1 outsider and was ridden by Seamus Durack, with Fitzgerald partnering the Henderson stable's more fancied runner Back to Ben Alder.

Trabolgan produced by far his best performance up to that time, moving up to challenge for the lead in the straight and finishing second by half a length to the Martin Pipe-trained favourite Liberman.

[7] In the 2003/2004 season, Trabolgan competed in Novice hurdle races, beginning at Aintree Racecourse in November where he started 11/8 favourite but fell at the sixth flight.

Fitzgerald moved the gelding up to dispute the lead three fences from the finish and Trabolgan drew clear of his opponents in the closing stages to win by two and a half lengths from Kadount.

Trabolgan overtook the favourite 150 yards from the finish, but Ollie Magern rallied to regain the lead in the final strides and won by a short head.

Four weeks later, the gelding started favourite for a novices' chase at Haydock Park, but was no match for the French-bred Jazz d'Estruval, who won easily by nine lengths.

[12] Trabolgan began his 2005/2006 campaign on 26 November in the Hennessy Gold Cup, a handicap race over three and a quarter miles at Newbury, in which he was matched against more experienced chasers.

[13] Following his victory at Newbury, Trabolgan was regarded as a leading contender for the 2006 Cheltenham Gold Cup and was expected to reappear in the King George VI Chase at Kempton on Boxing Day.

On 4 March he started favourite for a veterans' handicap at Newbury, but made several jumping errors and finished a distant fourth behind Eric's Charm.