Native Upmanship made his racecourse debut in a National Hunt flat race in February 1998 at Gowran Park, where he finished third behind subsequent Champion Bumper winner Alexander Banquet.
He had one more run that season in April, where stepped up on his debut, to win a National Hunt flat race at the Punchestown Festival.
His trainer stepped him up to the top level a month later for the Royal Bond Novice Hurdle, and Native Upmanship finished seventh of eight runners, behind Alexander Banquet.
In his final run of the season, Native Upmanship went to the Punchestown Festival, where he was sent off an 8/1 chance for the Land Rover Champion Novice Hurdle and won by 5 lengths.
In his final two starts of the season, when pulled up in the Irish Hennessy Chase and fourth in the Gold Cup at Fairyhouse.
In his final start of the season, his trainer again stepped him up to 3 miles plus, for the Punchestown Gold Cup, where he finished second to Florida Pearl.