Mr Cunningham's premature death in 2007 from motor neuron disease has left a lasting impact on the rugby community.
Coach of the Havelock North Intermediate rugby team Conrad Waitoa said the game was personal for him.
"For me it's quite a big thing because he was one of my best friends."
Mr Waitoa said Cunningham was both inspired and inspiring.
"He was very passionate when he was a rugby player helping these boys.
"So he would come to these games or he would go to their trainings. He embraced being a young person and seeing how the people he looked up to would help him out."
Mr Waitoa also said the game was not about winning.
"We're going to play the way he used to love playing. Today I just said to the boys, 'Enjoy it'."
Coach of the Heretaunga Intermediate rugby team and former coach of Cunningham, Kim Whittington, said: "He was a striver. He never gave up. It's all the values that we try to instill in our kids.
"Jarrod was a great guy with a great personality and a hard worker - and that's what we want our kids to be."
The boys were aware of how much Cunningham and the trust he generously set up had helped and shaped the sports community they were involved in.
"It's the least we could do for him. They'll have that in the back of their minds when they are playing today - even though we are from the west side of town," Mr Whittington said.
Parent David Gallagher also said the trust had been beneficial to the community.
"Even in death he is still doing a lot for Hawke's Bay rugby. I've explained [to my son] what Jarrod did for Hawke's Bay rugby. He really took it on board."
Cunningham's sister, Jane, said the trust was making a difference. "The money he left has made a huge impact. We've helped so many kids.
"We're still fundraising to keep it active."
