In Chile (1990-1991)

Wolf debuted as a two-year-old on April 29, 1990, in a 1300-meter maiden race at Club Hípico de Santiago,^[8] which he won by five and a half lengths.^[1] A month later, he easily won the Group 3 Clásico Raimundo Valdés C. over 1600 meters,^[8] with a winning margin of nine lengths.^[1]

Wolf's third race was the Group 1 Clásico Alberto Vial Infante, also 1600 meters long. Along with being his first start at the highest level of racing, it was his first start on a yielding track, since all of this other starts were run under firm conditions. He didn't handle the yielding track well, with his trainer José Tomás Allende Fernández saying that he dropped in level on the surface. Wolf struggled in the race, but managed to defeat Mayfair by one and a quarter lengths.^[1]

Wolf returned to the races as a three-year-old in the Group 1 Clásico Nacional Ricardo Lyon, run over 2000 meters. He ran in fifth place in the early parts of the race before moving to the lead 400 meters from the finish,^[7] pulling away to win by an authoritative eight and a quarter lengths.^[1]

A month later, Wolf ran in the Group 1 Clásico El Ensayo, one of the most important races on the Chilean calendar and first leg of the Chilean Triple Crown. Ten rivals faced Wolf, including Mayfair, who took the early lead in the 2400 meter race. Wolf ran the same way he did in the Clásico Nacional Ricardo Lyon, waiting in fifth place before making his move around the final turn.^[7] Once again, Wolf pulled away easily, winning by seven and a quarter lengths^[1] and setting a new track record^[3] of 2:23.1.^[9]

The Group 1 Clásico St. Leger, second leg of the Triple Crown, was Wolf's next race, run on December 1, 1990. It was his first race at a different track, Hipódromo Chile, and his first race on the dirt. The favorite for the race was Memo, then considered the best horse in training at Hipódromo Chile. The confrontation between the two colts was built up as the 'race of the century', with nearly one hundred thousand people attending the race.^[1][3][7]

As per his usual, Memo took the lead right out of the gates, but Wolf's jockey Luis Muñoz Ibáñez rode him much closer to the pace than usual, in third place, to avoid giving Memo too much of an advantage early on.^[1] Wolf moved into second place a little over 900 meters from the finish, and Luis Muñoz Ibáñez pushed him to stay on Memo's heels, despite so much of the 2200 meter race still being left to run. Coming into the homestretch, Wolf drew up next to Memo, and the two dug in for the final 400 meters. The two drew away from the rest of the field, by over twenty lengths.^[1] The two remained neck-and-neck until the final 150 meters,^[7] when Wolf began to open up on Memo, eventually winning by a length and a three-quarters.^[1] Afterwards, Wolf's trainer José Tomás Allende Fernández said "This is the loveliest race I have ever seen in my life."^[7]

Wolf returned to Club Hípico de Santiago later that month to run in the Group 1 Gran Clásico Coronación, run over a distance of 2000 meters.^[8] He won the race by nine lengths^[1] in a "walk".^[7]

The third and final leg of the Chilean Triple Crown, the Group 1 Clásico El Derby, a 2400-meter long race at Valparaiso Sporting Club, was run February 3, 1991. Wolf was a strong favorite become the first horse since Prólogo in 1966 to win the Triple Crown, despite the return presence of Memo. Wolf performed as expected, and the race unfolded much like the St. Leger, although this time Wolf crossed the finish line five lengths ahead of Memo.^[3]

For his campaign in 1990 and 1991, Wolf was named the Chilean Champion Turf Two-Year-Old, Champion Turf Three-Year-Old, Champion Dirt Three-Year-Old, and Horse of the Year.^[1]

In the United States (1991-1992)

Wolf's American campaign began July 29, 1991, in a mile long allowance race run over the Del Mar turf. Neil Drysdale had taken over training, and jockey Gary Stevens rode Wolf. Wolf was fractious and trailed the field for most of the race before rallying to finish second by two lengths.^[10] On October 4, he ran in a mile and one-eighth allowance at Santa Anita and won by three-quarters of a length.^[11]

Wolf then progressed to stakes races, running in the Grade 2 Citation Handicap, run over one and one-eighth miles on the turf at Hollywood Park, on November 30. Assigned 119 pounds, he was the co-highweight with Best Pal and two other entrants. Wolf ran third, just under two lengths from the winner.^[12]

Wolf didn't race again until September 10, 1992, when he contested a mile and one-eighth allowance race on the turf at Woodbine. He won handily by a half length.^[13] On October 4, he ran in the Grade 2 Niagara Handicap, one and one-quarter miles on the turf, as the favorite and highweight, assigned 117 pounds. He ran at the back of the field before making up ground late, but only managed to finish fourth.^[14] Two weeks later, he ran in the Grade 1 Rothmans Ltd. International Stakes over one and one-half miles on the turf. He made a bid, but hung in the late stretch to finish fourth.^[15]

Twelve days later, Wolf ran again, this time in the listed Prized Handicap, run over one and three-eighths miles at Gulfstream Park. He was the favorite and 117-pound highweight, but only managed a mild rally in the stretch, finishing fifth of ten.^[16]