As a 100/1 shot, Dark Side was certainly the roughie of the field in the running of the West Diggers Tamworth Pace (2360m) at Tamworth Paceway, but he came up trumps.
Maddison Simon took the drive for her grandfather and trainer Len Simon behind the Mach Three nine-year-old gelding, owned and raced by Maureen Simon, Len's wife.
"I held the lead and was hoping for the best - hoping that he could hold it all the way, and he did," Maddison said.
"Once we all settled down into the race, I was just hoping to hold that lead."
Dark Side notched his third win for the season, with Maddison guiding him to two wins in October last year over 1980m.
"He [Len] said that he [Dark Side] worked well in track work this week and I didn't really believe him but he was right," Maddison said.
The race certainly had some challenges for Dark Side, who had commenced from the three barrier.
Dark Side had opposition not long after the start, with the first lot of pressure coming from the Clayton Harmey-trained Choisir Damoure (Jake Hughes).
That was followed by $2.40 race favourite Azur Express (Blake Hughes), before Got The Scoop (Anthony Varga) applied pressure on Dark Side.
Another challenge came from the Tony Missen-trained Are You With Me (Tom Ison), who put in a three-wide run from the back of the field just before the bell sounded.
"He (Are You With Me) got his head in front on the final turn," Maddison said. "I was a bit concerned then but Dark Side just come through and held on."
She added: "We were both head to head down the home straight."
Art I Special (Scotty-Jon Welsh) was 2.4m away in third place.
Maddison picked up the The Pub Group Drive of the Night.
With the lifting of the regional racing zones last Wednesday, the base prize money has increased from $4000 to $6000.
It had been at $4000 since May 11 because of the coronavirus pandemic.