2006
In 2006, he made All-Australian selection, and was once again selected to represent Australia in the International Rules series. He had a highly successful series, scoring more points than any other player. He was awarded the Jim Stynes medal for the best Australian player in the series.
O'Keefe played his 100th AFL game in Round 7 against Richmond. In what was also Paul Williams' 300th game, Sydney defeated Richmond by 118 points.
He came equal second in the running for the Bob Skilton Medal, which is annually awarded to the Best and Fairest player at the Sydney Swans, to one of the three Co-Captains, Brett Kirk.
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