About 50 cyclists rode the 71km distance from Gore to Invercargill in the Stonewood Homes Gore to Invercargill race on Saturday.
Cycling South Marketing manager Eugene Bonthuys said the race was first run in 1930, and the trophy featured some top names in the sport.
This means that the fastest riders, who start in the "scratch" group, have the biggest deficit to make up, giving everyone the chance to cross the line in first place.
The first cyclist who crossed the line in Invercargill was 16-year-old James Gardner, of Dunedin, who was also the fastest under-19 rider.
"I always ... enjoy that side of things. Racing comes second ... the joy of training hard is racing becomes something fun ... to look forward to."
The victory was even more special as it was during his last holiday weekend, a good start for his school year, he said.