But as he prepares to celebrate the milestone, the Manly captain has insisted he would not do anything differently if given his time over.
When the Sea Eagles face St George Illawarra in Wollongong on Saturday, Cherry-Evans will become the 49th player to reach 300 games and only the second after Cliff Lyons to play that many for Manly.
The 34-year-old has instructed the club to keep fanfare to a minimum as the Sea Eagles focus their energy on keeping their slim finals hopes alive.
But allowing himself to reflect on his career, Cherry-Evans believed he could be proud of the way he navigated the windy road to 300 games.
In only his 27th first-grade game, 22-year-old Cherry-Evans won the 2011 grand final as one half of the NRL era's youngest premiership-winning halves pairing.
He has gone on to enjoy a storied career for club, state and country, captaining Queensland to victory in three State of Origin series and representing Australia 18 times.
"At the very start of my career, I was very ambitious about playing a lot of first-grade, not just one game," he said.
"But I probably have outdone my expectations as a 12-year-old kid.
"My journey hasn't been plain, I reckon I've had a pretty up-and-down ride. A lot of that is from your own doing."
Cherry-Evans' early days at the Sea Eagles were marked by a rift with older teammates who had been part of Manly's 2008 premiership, notably Anthony Watmough and Brett and Glenn Stewart.
"I've had my prickly moments with teammates over the years, I've never shied away from that," Cherry-Evans said.
And in 2015, Cherry-Evans caused a stir across the league for agreeing to join Gold Coast before reneging to re-sign long-term with the Sea Eagles.
"You guys (the media) gave me a fair bit of grief," Cherry-Evans said.
"It made me understand who I could trust and who was closest to me. In your hardest times, you find those things out."
Cherry-Evans was willing to take the tests with the triumphs, lauding the Manly club for its support through it all.
"I don't think I'd change a thing because I'm really content with the career and the person I've become," he said.
"(Manly) has given me so much, it gave me my opportunity, it's backed me, and I like to think I've repaid that with some really good footy over the years."
Contracted through 2025, Cherry-Evans is in some of the best form of his career despite his age but believes he is unlikely to challenge Cameron Smith's league record of 430 games.
"If anyone goes near that record, then well done to them," he said.
"I can't say my ambition goes that far."
Manly are one point out of the top eight but in the thick of a logjam towards the middle of the ladder so each of their final six games will be crucial to their finals hopes.
"I don't think I've won at WIN Stadium so maybe this (the 300th) is the special thing that we need to get the win," Cherry-Evans said.
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