The club called off contracts talks with Cloke during the season but has quickly ironed out the finer details of the deal following the Pies' exit from the finals at the hands of Sydney on Friday, with the 25-year-old securing a new contract with a conditional fifth year.
Cloke's deal will almost certainly see him finish his career in the black and white, while fellow premiership player O'Brien has signed on until the end of 2014.
Collingwood director of football Geoff Walsh said the deal was great for both parties and reflected Cloke's value to the club.
"It's obviously a long commitment from both parties which, from our point of view, reflects the regard we hold Travis in and our faith in his ability to play good football for a long time to come," Walsh said.
"I think it's also a reflection of Travis' regard for Collingwood. He said all along that he wanted to stay at the Westpac Centre and clearly he's prepared to make Collingwood his football home for many years."
Walsh admitted the process had been long and arduous and confirmed the fifth year would have conditions.
"Although the negotiations have been protracted all parties - Collingwood Football Club, Ralph Carr of RCM Sport, David Cloke and the Cloke family - have always been working towards the common goal of Travis remaining a Collingwood player," he said.
"The final year is not unencumbered. There are conditions that will remain a matter for Collingwood and Travis but clearly both parties are comfortable with them."
A 2011 All Australian, Cloke struggled to recapture his form this season as negotiations dragged on, but turned it around with two of his best games against Essendon in Round 23 and Hawthorn in the qualifying final, bagging a combined 11 goals.
Cloke played all 25 games for Collingwood this season, taking his career tally to 174 over eight years and was the club's leading goal kicker for the last two seasons with 69 and 59 goals respectively.Meanwhile O'Brien, also 25, has managed 159 games across eight years having started out as a rookie in 2005.