The dual Magpies premiership hero's announcement on Thursday comes just hours after Richmond midfielder Dion Prestia ended his Tigers career less than a kilometre away at Punt Rd.
Debuting in 2009, Sidebottom has played 373 AFL games - the second most in Collingwood's storied history, only behind Scott Pendlebury.
A member of the Magpies' 2010 premiership side as a 19-year-old, Sidebottom then kicked a famous goal late in the 2023 grand final to help seal the club's next flag 13 years later.
With Collingwood guaranteed to be in the wildcard round of the finals, at least, Sidebottom will be hoping for a fairytale farewell.
The versatile midfielder won the Magpies' Copeland Trophy in 2017 and 2018, also earning All-Australian honours once.
"As a young kid from 'Tally' (Tallygaroopna), I could never imagine I'd finish my AFL career with over 370 games, two premierships and 18 years of memories," Sidebottom said.
"When I look back on my time at Collingwood, I'll remember the people.
"So many teammates, coaches, staff and volunteers have invested their time and energy into helping me along the way."
Collingwood coach Craig McRae hailed Sidebottom's influence, saying his "football speaks for itself".
"His consistency, professionalism and ability to perform under pressure have been remarkable throughout his career," McRae said.
"But for me, his greatest strength is his character.
"He's authentic, caring, humble and has a wonderful way of bringing people together."
Sidebottom might not be the only senior Collingwood player to retire this year, with Pendlebury also weighing up his future after breaking the VFL/AFL games record in May.
The Magpies have the oldest list in the AFL and are attempting to stay in premiership contention with a group in transition.
At Richmond, Prestia has joined premiership teammate Nathan Broad in exiting the Tigers from their golden era.
Despite Richmond announcing he was retiring, Prestia is giving serious thought to continuing his AFL career at GWS next year.
Giants coach Adam Kingsley spent years as an assistant coach at Richmond with Prestia.
"I made sure I didn't put the r-word (retirement) into my announcement!" Prestia told SEN on Thursday.
"I'm still leaving the door open a little bit. I'm feeling pretty good still, body-wise and mentally."
Starting his career at Gold Coast, Prestia enjoyed instant success after making the switch to the Tigers in 2017.
The midfielder played in three premierships (2017, 2019, 2020) in his first four seasons at Richmond.
Despite being riddled by injury in 2020, and restricted to just five games during the COVID-affected season, Prestia returned to play an important role in all four of the Tigers' finals.
Prestia and Broad will be given a farewell in front of the Richmond army this Saturday when the Tigers host St Kilda at the MCG.
"I've had some conversations with the club over the last two months and decided that it's a good opportunity to finish up at the 'G with my two very good mates, with Nathan Broad (retiring) and Tom Lynch playing his 250th," Prestia added.
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