He is a two-time winner of the Australian Open and late in his career eventually won a PGA Tour event, the 2016 Barracuda Championship.

He defeated Robert Allenby and Marcus Fraser in a sudden death playoff to take the title.

In December 2014, Chalmers won his second Australian PGA Championship title in a sudden death playoff.

Woodland bogeyed the last hole and Chalmers eagled the par-five 18th, which meant a six-point victory under the tournament's Modified Stableford scoring system.

Chalmers finished 142nd in the FedEx Cup and did not qualify for the postseason, but the win made him fully exempt through the 2017–18 season.

Chalmers was unable to follow up his win and cut his 2018 season short due to arthritis in his back.

He made no starts in 2019 and played with a Major Medical Extension until 2020, when he was unable to meet the terms and was demoted to the Past Champions Category.

1Cancelled due to 9/11 QF, R16, R32, R64 = Round in which player lost in match play "T" = Tied NT = No tournament Note that the HSBC Champions did not become a WGC event until 2009.