It started in 1976 when city and country school exchanges were common.
Fast forward to 2014 and Wauchope Day is still the No. 1 event on the Cumberland High School calendar.
The Carlingford school will host 100 students from Wauchope High School, on the NSW mid-north coast, for three days of sports and social activities from June 25.
Year 7 student Emilio Guttierez will compete for the first time in soccer and athletics for the Jack Parsons Memorial Shield, named after the bus company proprietor and Wauchope High School supporter who donated it when the exchange began.
"I've been in a grand final but I'm not sure which is better," he said.
"I'm excited. People have told me that it's intense and fun and competitive."
Year 12 student Brendan Heang will play soccer, basketball, rugby league and other sports in the tournament for a final time.
He was also in the team when Wauchope hosted the event last year.
"It's so much fun, everyone looks forward to it," he said.
"It's what we train for. I'm a bit nervous because we haven't won since I've been here, but excited."
PDHPE head teacher Clarinda Brown said the event had lasted 39 years because of community support.
"The 100 students who travel each year, whether to Cumberland or up to Wauchope, are billeted by families,'' she said.
"It doesn't work without the family support.
"The event is the longest-running of its kind in the state. It initially started to have bit of a cultural exchange between a country school and a city school and it has continued on from there."