In this first match in 1897, Yale prevailed, besting Princeton in the first round, and then Harvard in the finals. The following year had the same results, sending the Ardsley Cup back to New Haven.
In 1898, the IGA decided to switch the competition from the spring season to the fall, so, 1898 had two competitions. In October, the tournament was played once more, with Harvard and Yale meeting in the final round for the third year in a row. In the closest match up in the tournament’s short history, Harvard claimed the victory, blocking Yale from claiming the Ardsley Cup for good.
The fourth year of tournament play brought the first time Harvard and Yale did not play each other in the final round, after Princeton won the first round. During the Harvard-Princeton final, the Crimson were victorious for the second year in a row.
After it was decided to move the competition back into the springtime, 1900 did not see any intercollegiate play. However, by the time 1901 came around, Penn finally joined the matchup. With a preliminary match added to account for the extra team, two teams were selected at random for an extra round of golf. Harvard beat Princeton in the preliminary and Columbia in the next to meet up with Yale once again in the final.
As both teams needed to secure a third victory to claim the Ardsley Cup, this matchup would end in a dramatic fashion. Harvard, however, was able to best Yale, solidifying their claim to the historic trophy.