Pitman, who trains with his son, Matthew, is on the cusp of an unprecedented milestone in New Zealand thoroughbred racing history in the new millennium- provided the horses follow suit.
''We might time our run to a nicety because we're three wins off training 1000 winners this century,'' Pitman said.
If they go half as well as they did at last year's New Zealand Cup carnival, they will reach the milestone by the last day of the carnival on November 14.
''We won six last year. That'll be a hard act to follow but we'll be trying hard.''
The Pitmans' team has been conspicuous by its absence on some of the smaller days around the South Island so far this season - a planned move. ''I've hardly raced any horses on industry days and we've concentrated on feature meetings,'' he said.
''They've been tough, but hopefully our horses have a little bit of improvement in them in a fortnight's time.''
Son Of Maher is one horse Pitman expects improvement from, despite an excellent second behind Risque in the listed Armadillo Stakes at Riccarton on Saturday.
The Al Maher gelding's placing over 1600m on Saturday should confirm his spot in the New Zealand 2000 Guineas on November 7, although Pitman thinks the 1600m will be short of the 3yr-old's best.
''I don't think he's a guineas horse, but he's earned his place in the field so he's running. He's a Derby horse rather than a guineas horse - he wants further. He could run in a 2000m race tomorrow - that's the kind of horse he is.''
Lisa Allpress has been engaged for the group 1 feature on the first day of the carnival.
Pitman rates the 3yr-old highly, and even stepped away from his usual philosophy when he felt the colt was not right after his fourth at Riccarton on October 3.
''I hardly ever take blood tests - I wouldn't take one [more than] every three or four years - but we took a blood off him and it was perfect, except he had a high muscle [enzyme] count,'' he said.
''We treated him for it but we had to be a little bit careful so he'll have a little bit of room for improvement.''
Southern Sav copped a hefty eight-point ratings penalty for the New Zealand Cup for running second to The Bishop
in the Spring Classic, which Pitman felt was ridiculous.
''I was surprised at the penalty he got the other day for running second - in fact, I'm still arguing the point with the handicapping staff.''
Pitman is not concerned whether the 6yr-old makes the New Zealand Cup field.
''I don't want to punish him because I think he'll be a better horse come Christmas. He's running the first day in the mile and a-half [Metropolitan, over 2500m]. If he runs one, two or three we will run him in the cup.''
Another Coup was taken out of the Coupland's Mile nominations prior to the second withdrawals yesterday morning and will head to the group 3 Canterbury Breeders Stakes on the middle day.
The 11yr-old, El Chico, will either head to the group 3 Stewards Stakes on November 11 or the open 1400m at Wingatui on Tuesday.
''The main race for him is the 1400m on the last day and he has backed up from the Stewards to the 1400m well in the past.''