John Wheeler is a great trainer with a great philosophy - which makes him well suited to jumps racing.

"You go into this with hope, but not with expectations," Wheeler said.

"It's tough and it hurts sometimes, but it's not bad fun.

"A bit like life."

Wheeler has won four Grand Annual Steeplechases - and has also seen one of his favourites tumble over at the first.

At Warrnambool on Thursday he will keep his expectations in check as he saddles up Tobouggie Nights and Banna Strand in Australia's longest and most gruelling horse race.

Wheeler, a New Zealander without whom Australian jumps racing would be all but lost, has been a Grand Annual stalwart for almost 30 years.

"I used to hear stories about this place so I came and had a look and now you couldn't keep me away," he said.

Until Tuesday, Tobouggie Nights had been Wheeler's better prospect. But Banna Strand, a horse famous for jumping into the crowd during the 2011 Grand Annual, finished second in Tuesday's Brierly Steeplechase.

"They're both going to have to produce their best runs to be in it this year, but if they did that, and a few other things go their way, they could get into it," Wheeler said.

Last year's winner Awakening Dream and the Great Eastern Steeplechase winner Man Of Class are battling for Grand Annual favouritism with the Wheeler pair at around $7.

In the feature flat race of the week, the Warrnambool Cup (2350m), increasing confidence is accompanying the bid of another trainer establishing himself as a stalwart of the three-day meeting.

Local horseman Jarrod McLean, who won Tuesday's Brierly Steeple with Cat's Fun will run King Diamond in Thursday's Cup.

The winner last November of the Ballarat Cup, King Diamond is having his third run from a spell at Warrnambool.

But McLean has put the work into his horse and is confident a lack of racing won't be a problem.

"He looks terrific now and this is his target, we've set him for this race all along," McLean said.

Tasmanian Banca Mo is favourite for the Cup at $3.10 with King Diamond a $13 chance.