In June 2008, after playing 26 games in a season and a half, he underwent back surgery to repair a prolapsed disc, missing the rest of the year.[3] He returned the following season to have one of his best seasons,[2] earning 10 Brownlow Medal votes to be the equal leader for Essendon and finishing fifth in the club's best and fairest award.[4]
In round 4, 2011 Winderlich suffered a serious ACL injury which ended his 2011 season.
In August 2014, Winderlich announced he would retire at seasons end; however, after the end of the Essendon's finals campaign, it was publicly revealed that he was contemplating playing on. After reports he had chosen to continue his career at Richmond,[5] Winderlich announced in October that he would be staying with Essendon to continue his career.[6] He managed only one match for 2015 due to a back injury, and he announced his proper retirement in September.[7]
Post-AFL
On 3 August 2024, Winderlich suffered a spinal injury while playing for Thorpdale in the Mid Gippsland Football Netball League (MGFNL). Winderlich took a knock to the head after collecting the ball during the second quarter, and had to be flown by helicopter to The Alfred Hospital in Melbourne.[8] The game, which was being played against Toora, was abandoned.[9]
