2006

Pendlebury's 2006 pre-season was hampered by glandular fever, but he made a successful comeback with Collingwood's VFL affiliate, Williamstown. He made his AFL debut in Round 10 against the Brisbane Lions, and became part of a select group of footballers known for kicking their first goal with their first kick in league football.^[8] He played eight more games in the 2006 season.

2007

Pendlebury switched to the number 10 guernsey previously worn by Blake Caracella, and gave the number 16 guernsey to newcomer Nathan Brown. Following his nine games in 2006, Pendlebury broke into the Collingwood midfield on a regular basis, averaging 18 disposals a game before he was nominated for the NAB Rising Star in Round 4. He collected a season-high 26 possessions in the 2007 Semi-Final against the West Coast Eagles in Perth, and kicked a crucial goal during extra time.^[9]

Throughout the 2007 season, he was compared with Geelong rookie midfielder Joel Selwood.^{[by whom?]} Both were close favourites for the 2007 NAB Rising Star with Selwood eventually winning by seven votes.^[10]

Pendlebury also placed second in the 2007 Copeland Trophy behind Travis Cloke.

2008

Pendlebury was voted into Collingwood's five-man leadership group as deputy vice-captain preceding the 2008 season.^{[citation needed]}

Highlights of Pendlebury's season included 33 disposals against Essendon on ANZAC Day and placing a close second behind Paul Medhurst for the Anzac Day medal.^{[citation needed]}

On 9 May 2008, Pendlebury was selected in the Victorian Squad for the AFL Hall of Fame Tribute Match, with teammates Josh Fraser and Heath Shaw. Despite playing only half of the match, he collected 19 disposals with a 79% efficiency rating.^[11]

Pendlebury was an important factor in Collingwood's 86-point victory over reigning premiers Geelong.^[12]

Pendlebury played his 50th game on 9 August 2008 against St Kilda in Round 19. He finished third in Collingwood's 2008 Best and Fairest count.^{[citation needed]}

2009

This section of a biography of a living person does not include any references or sources. (April 2014)

Pendlebury became more prominent in 2009. He collected a career high 39 disposals against Melbourne Football Club on the Queens Birthday and won the Women's Round medal. He had a career high 22 kicks against the West Coast Eagles and another career high 20 handballs against the Richmond Football Club. Despite missing a few games due to injuries, he was still shortlisted for selection as an All-Australian. He had an average of 26 disposals a game (13 kicks and 13 handballs)and averaged 2 goals per 5 games. His season ended with a cracked fibula bone injury in the Qualifying final.

Pendlebury polled 13 votes in the 2009 Brownlow Medal, the top ranked Collingwood player.

2010

In 2010 Pendlebury won a spot in the All-Australian team^[13] and won the ANZAC Medal. He polled 21 votes in the 2010 Brownlow Medal, to finish in fourth position.^[14] He won the 2010 Norm Smith medal when Collingwood won the premiership.

2011

In 2011 Pendlebury won his second ANZAC Day Medal as best-on-ground in Collingwood's 30-point win over Essendon.^[15] Three weeks later, against Geelong, he was controversially denied a goal from a free kick that would have won Collingwood the game. Ultimately, the Magpies lost by three points.^[16]

He capped off a brilliant year, winning the Copeland Trophy for the best and fairest player at Collingwood, and the Bob Rose Trophy for being the best Collingwood player throughout the finals.^[17]

In the Brownlow he polled 24 votes to finish equal third behind winner Dane Swan, Sam Mitchell (disqualified) and Nick Dal Santo.^{[citation needed]}

2012

Pendlebury finished the season with 15 brownlow votes, down on his 24 from the previous year and helped the Magpies to a Preliminary Final, where they eventually lost to the Sydney Swans. He finished second in the Copeland Trophy to winner Dayne Beams and in front of three-time champion Dane Swan. He was also included in the All Australian for the 3rd year running alongside teammates Swan and Dayne Beams.^{[citation needed]}

2013

This section of a biography of a living person does not include any references or sources. (April 2014)

Pendlebury improved on his 2012 season, having arguably his best and most consistent season to date. Already touted as future captain of the Collingwood Football Club, Pendlebury helped lead the club brilliantly in 2013 and although Collingwood lost the Elimination final loss to Port Adelaide, Pendlebury won his second Copeland Trophy beating former champion Dane Swan. He also had 21 votes in the Brownlow, only losing out to teammate Dane Swan for the highest votes for the Magpies. Pendlebury once again was included in the All Australian Squad being named on the wing. This was his fourth consecutive inclusion in the team.

2014

On 29 January, Pendlebury was appointed as captain replacing Nick Maxwell.^[18] Pendlebury has thrived as captain having one of his best seasons.

At the end of the season, Pendlebury was selected for the fifth consecutive time as part of the All Australian team^[19] and was awarded the Lou Richards Medal. He also won his third Copeland Trophy, the Magpie Army Player of the Year award and the Gavin Brown Award.^[20]

2015

During the 2015 Copeland Trophy event, Eddie McGuire announced that Pendlebury had re-signed with Collingwood until the end of 2020. Pendlebury said at the event: "The direction the club is taking really excites me. We have a solid group of young players who have got a taste of senior footy and we have the right program and people in place to take this group to the next level. I’m proud to captain this club and want to be part of what the future holds."^[21] The same night, he won his third consecutive Copeland Trophy and fourth overall.^[22]

2016

Pendlebury battled injury early in the season as well as filled in as a half-back instead of his regular role in the midfield; despite this, he maintained his consistency. His professionalism and inspiration prompted his peers to vote for him as the winner of the Gavin Brown Award for demonstrating the team values throughout the season.^[23] He was further rewarded with his fourth consecutive Copeland Trophy and fifth overall.^[24][25]

2017

Pendlebury had a consistent 2017 season until he sustained a broken finger in Round 17 against the Gold Coast Suns. He had successful surgery on the finger, and was hopeful to return the next week, but his return was delayed for a month and it was said to be unlikely that he would play again until Round 22 or 23. However, did not return again for the season. In the 2017 season, he averaged a career high tackles per game (6.4).^{[citation needed]}

2020

In round 18 of the 2020 season, he broke the Collingwood record for most VFL/AFL games played, as well as most games as captain.^[26]

2023

Pendlebury resigned his post as captain of Collingwood after the 2022 AFL season.^[27] In Round 17 of the 2023 AFL season, Pendlebury broke the VFL/AFL all-time disposal record, surpassing Robert Harvey.^{[28][29][30][31]}

As a premiership player in the 2023 AFL Grand Final, Pendlebury broke his 13-year-long premiership drought, alongside Steele Sidebottom, which is a league record between premierships.^{[citation needed]} This game also saw Pendlebury draw level with Gordon Coventry for the most AFL finals played at Collingwood, with 31 apiece.^[32]