The in-form Malaysian rider landed his one and only Derby in 1992 with Peak Of Perfection XI when he was then apprenticed to the winning trainer Malcolm Thwaites.
The closest the 45-year-old hoop has since come to capturing a second Derby was with trainer Desmond Koh's honest mare New Rose Wood in 2010, finishing only three-quarter length off the winner Race Ahead.
It's been more misses than close hits since, but Woodworth has a good hunch about the Mark Walker-trained Sacred Croix in next Sunday's $1 million Group 1 Singapore Derby (1800m).
The son of Savabeel ran second in the first two Legs of the Singapore Four-Year-Old Challenge, beaten in almost carbon-copy style by Cliff Brown's bonny mare What's New.
With the extra 200m from the first Leg, the Group 3 Silver Bowl (1400m), Sacred Croix was actually favoured to turn the tables on What's New in the second Leg, the Group 2 Stewards' Cup (1600m) on June 30, but after doing extra time three wide, his acceleration seemed bereft of punch.
It's only in the last 100m that the Dato Yap Kim San-owned gelding went through his gears, but What's New was home and hosed.
Woodworth said Sacred Croix, whom he rode to a four-in-a-row that vaulted him from Open Maiden company to Class 3 level in the space of two months, was a typical Savabeel who will reach the peak of his powers over longer trips.
"He was unlucky with his draws in the first two Legs," he said.
"He was beaten in second place on both occasions, but he has improved a lot with each run.
"He has actually improved with each run as he's risen all the way to the top from the bottom class.
"He's done nothing wrong that's for sure, and he will definitely handle the 1800m even if it'll be his first time.
"I hope his luck can change in the race that matters the most. It would be my second Derby if he wins as I won on Peak Of Perfection XI in 1992.
"I then finished second once with Desmond's mare (New Rose Wood). It's an open Derby this year, and I hope my horse can go one better."
Woodworth is a talented jockey but went through a rollercoaster ride during the time he plied his trade between Malaysia and Singapore in the mid-noughties.
But from journeyman, he has turned into a jockey in red-hot form this year, with the defining turning point being the Group 1 Dester Singapore Gold Cup (2000m) with Elite Invincible last November.
Support from Walker – who sparingly used Woodworth then - Elite Invincible's trainer, has increased manifold since, to the point the on-song duo team up more often than the old lethal Walker-Vlad Duric combination.
Out of Woodworth's 27 winners this season, 16 have hailed from the two-time Singapore champion trainer. Woodworth is enjoying one of his best Kranji seasons of all time this year, sitting in third spot, albeit the 21-win margin on leader Duric looks almost impossible to bridge.