The ladder-leading Magpies are favourites to win their first AFL flag in 13 years after backing up their extraordinary 2022 surge under head coach Craig McRae.
As Sidebottom prepares to become just the fourth Collingwood player to reach 300 games, the 32-year-old reflected on becoming a premiership hero as a teenager.
"I remember being told at an early age to really make the most of it because it doesn't happen that often - and I've found out since that was really the truth," Sidebottom said on Wednesday.
"I'm clearly a lot older now so I just make sure that everything I'm involved in I really just sit back and embrace it and take it all in.
"I'm clearly at the end of my career now and I'm running out of opportunities to play in big games.
"I guess it was great to win one so young but I would appreciate it a lot more if I was to win one before I was done."
Sidebottom said he still thinks about Collingwood's last-gasp 2018 grand-final defeat to West Coast "a lot".
"What I went through in the first few years of thinking finals is going to happen all the time, whereas I'll just remember even things like the parade (in 2018) really just taking it all in and being grateful for the position that I was in," Sidebottom said.
"I feel like I'm in debt to the footy club. I hope I've been able to repay the faith that they showed me.
"I was a Bombers supporter growing up but I'll be a Magpies man forever now."
Sidebottom estimates 100 family and friends will be travelling from his home town of Shepparton to Marvel Stadium on Sunday for his milestone match against North Melbourne.
Long-time teammate Scott Pendlebury has streaked away as Collingwood's games record-holder in recent years but Sidebottom also joins Magpies royalty Tony Shaw and Gordon Coventry in the 300-club.
Sidebottom and Pendlebury have won 170 games together - the most of any two Collingwood teammates.
"There's been a lot of people along the way that have helped me to get in the position that I'm in," Sidebottom said.
"I hope they can get some enjoyment out of it just as much as I have throughout my whole career."
COLLINGWOOD GAMES RECORD LIST
1. Scott Pendlebury 367*
2. Tony Shaw 313
3. Gordon Coventry 306
4. Steele Sidebottom 299*
5. Wayne Richardson 277
(* denotes: Still playing)
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