[3][2] Freire debuted at age two on February 12, 1930, in the 800-meter Premio Campanzo at Club Hípico de Santiago, facing five others.
Freire won by one and a half lengths, defeating well-regarded racers such as Big Notice, Weimar, and Bodas de Oro.
In the Chilean Polla de Potrillos, run over 1400 meters on August 24, Freire took the lead at the head of the stretch and pulled away to win by eight lengths.
[3] Only five other horses came to face Freire in the 2400-meter Clásico El Ensayo, first leg of the Chilean Triple Crown, on a rainy October 19, 1930.
[3] Freire was brought to Viña del Mar and the Valparaíso Sporting Club for the Clásico El Derby, second leg of the Chilean Triple Crown, which he won by two and a half lengths.
Cáceres let Freire run freely, and he won by 10 lengths in a time of 1:351⁄5 for the 1600 meters, breaking the previous record set by the noted racehorse Old Boy that had stood for 16 years by 2⁄5.
[3] After the Copa Jackson, Freire's soundness was less than ideal, so Cavieres prepared him for the final leg of the Chilean Triple Crown, the 3000-meter Clásico St. Leger, with gentle trotting and long walks.
The ruse succeeded, and Tantehue was withdrawn from the race, leaving Freire to walk over for the win and the Triple Crown.