Delighted just to be back on the European Tour he left in 1993 due to a lack of success, the 31-year-old from Devon was even happier after starting the Heineken Classic at The Vines here with a seven-under par 65. He goes into the second round level with the world No 5, Ernie Els, and only one behind the leader, Jarmo Sandelin of Sweden.
Winchester made his move with five successive birdies around the turn and then closed with another. Comparisons between him and Nick Faldo were inevitably made in 1985 when he won the English amateur title at the age of 18 - a decade after Faldo had done the same - and he took them a stage further.
"I tried to model myself on Faldo," he said. "David Leadbetter became my coach when I was at college in Florida and I used to play with Nick a bit. But I completely lost my way. I got far too technical and there were times when I wanted to give up because I was so confused with what I was doing.
"It was terrible financially too - it still is. I had a house in Wimbledon that I had to sell because I couldn't afford the mortgage and right now I'm renting a room in a house in London for pounds 40 a week.
"It's difficult to break even on the Challenge Tour and it was a huge relief to finish fourth on that last year and so give myself another chance on the main Tour."
Winchester has been helped by a renowned American sports psychologist, Bob Rotella, whom he wrote to in desperation. "I've learnt that everybody is different. I mean, you don't see Woosie trying to play like Faldo, do you? He's got his own personality.
"As long as I can keep doing the same thing day in, day out hopefully things will keep improving for me."
Sandelin missed Padraig Harrington's Vines course record by just one shot. Sandelin grabbed no fewer than nine birdies in a round he rated one of the best of his life.
However, Els is an even firmer favourite for the first prize of pounds 108,000 after collecting seven birdies himself. The winner of the South African PGA championship two weeks ago , Els is keen to keep pace with 59-shooter David Duval - a double champion on the US Tour already.
Scotland's Andrew Coltart opened with a 66 for a share of fourth place as he began his bid for a third success Down Under, having won the Australian PGA title in Sydney in 1994 and 1997.
This event counts for the Ryder Cup qualifying table and another win would probably get the 28-year-old into the 64-man field for the Andersen Consulting World Match Play Championship in California next month.
Currently seventh in the Ryder Cup table and 74th in the world rankings, Coltart matched Els by not dropping a stroke and scored six birdies in his last 12 holes.
Sam Torrance is 14 shots off the lead after requiring pain-killers for the shoulder injury which forced him to drop out of last week's South African Open.
Scores, Digest, page 29