From Bulbapedia, the community-driven Pokémon encyclopedia.
Drake holding the Winner's Trophy
The Winner's Trophy (Japanese: ウィナーズカップ Winner's Cup) is the prize for championing the Orange League. Only Pokémon Trainers skilled enough to defeat the Head Leader in addition to all four Gym Leaders in the Orange Crew can have it.
Trainers who earn the Winner's Trophy are honored in the Palace of Victory forever.
In the past
holding aloft his trophy 300 years ago
In A Shipful of Shivers it is revealed that Captain won an older version of the Winner's Trophy 300 years ago using his Gastly and Haunter.