Pendlebury is the league record holder for disposals, handballs and tackles,[2] and also has the most Brownlow Medal votes of any player who has not won the award.

[3] Originally from Sale in the Gippsland Region of Victoria, Pendlebury began his sporting career playing basketball and accepted a scholarship to the Australian Institute of Sport in Canberra; however, after three weeks at the AIS, he decided to quit the under-18s squad and return to Victoria to pursue professional football with the Gippsland Power in the TAC Cup.

Pendlebury's vacated place in the AIS squad was taken by Patty Mills, who went on to win an NBA Championship in 2014 with the San Antonio Spurs.

[8] Pendlebury's 2006 pre-season was hampered by glandular fever, but he made a successful comeback with Collingwood's VFL affiliate, Williamstown.

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.

[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.

He collected a career high 39 disposals against Melbourne Football Club on the Queens Birthday and won the Women's Round medal.

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

[citation needed] 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.

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.

At the end of the season, Pendlebury was selected for the fifth consecutive time as part of the All Australian team[20] and was awarded the Lou Richards Medal.

[23] 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.

[28] In Round 17 of the 2023 AFL season, Pendlebury broke the VFL/AFL all-time disposal record, surpassing Robert Harvey.

[citation needed] This game also saw Pendlebury draw level with Gordon Coventry for the most AFL finals played at Collingwood, with 31 apiece.

[39] Notes Team Individual * denotes rookie listed players * Leon Davis was replaced by Tyson Goldsack in the Grand Final replay