The Pioneer Pupil won a rating 80 2100m event by five lengths on a slow track at Washdyke.
His win came after four placings in a fresh campaign.
The Pupil gelding won over the Oamaru Cup distance, 2200m, at Oamaru last August.
King Of Jacks, a rival for The Pioneer Pupil, won over 2100m at Ashburton on July 6.
He ran second to First Wind in the Oamaru Cup two years ago.
First Wind is top weight tomorrow with 58kg.
He carried 57.5kg in his win when trained by Shane Kennedy and Ricky Carston.
The 7yr-old gelding is now in the Ashburton stable of Pam Gerard.
Joint Effort, who ran third to Flame Proof and Pasco in the Oamaru Cup last year, is also in the field tomorrow.
Trainer Michael Pitman has his last chance to overhaul Mark Walker in the trainers' premiership tomorrow.
Walker has 84 wins, one more than Pitman with the season ending on Thursday.
The Pitman-trained horses engaged tomorrow are:Race 1: Suzidiva.
Race 2: McConnell Road.
Race 3: Peyow Peyow, Square Pants, Our Genes.
Race 4: Driveallnight.
Race 5: The Pipi Pincher.
Race 6: Dr Zeuss, Shostakovich.
Race 7: Rhythm Master, Our Sheriff.
Race 8: Global Charmer.
Race 9: Jazzy Annie.
Race 10: Outback Fox, Rhythm King.
Mr Gilligan, a last-start maiden winner at Oamaru, has been scratched tomorrow.
His trainer Terry Kennedy, said the track would be too wet for Mr Gilligan.
Jeannot, Olivernotha and Balmuse have joined Waikeepadacash as late entries for the $125,000 Winter Cup at Riccarton today week.
The late entry fee was $2000.
Additional information for meetings today:Taumarunui RCRiders:Race 10: Can't Cash Sorry - N Harris; Hidden Destiny - K Hercock.
Scratchings:Race 2:Verago.
Race 6: Duthie Mills.
Race 8: Alabama Joan, Mauria.
Weather, fine; track, slow (9), rail out 6m.
Levin RC:Riders:Race 9: Beach Party - K Smith.
Form:Race 2, Lord Monty, 13th Wanganui Cup, Thursday; Jonbalena, sixth Wanganui Cup.
Scratchings:Race 2: True Power.
Race 3: Texas Hold Em.
Race 5: Brenna, Acid Jazz, De Lago Dancer,Race 6: Miss Salute.
Race 8: Quanah.
Race 9: Lawsuit.
Weather, fine; track, heavy (10); rail true.
