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Sam Kerr set to make history at Dolan Warren Awards

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NWSL Week 2 highlights (2:38)

Take a look at the best moments from NWSL week 2, including an eight goal thriller in Chicago. (2:38)

Matildas captain Sam Kerr could write a piece of Australian football history on Monday night at the Dolan Warren Awards in Sydney.

The awards night will bestow the Johnny Warren Medal to the A-League's best player, and the Julie Dolan Medal to their counterpart in the W-League.

Kerr, after another prolific season for Perth Glory, could be the first person -- male or female -- to win the most prestigious individual prize in Australian football three times.

The 25-year-old, currently in action for Chicago Red Stars in the NWSL, has already claimed the golden boot for her goals that took Perth to the Grand Final.

She is a strong chance to win the Julie Dolan Medal again, which would be her third straight; including a shared award last year with Matildas defender Clare Polkinghorne.

Another win for Polkinghorne would also be the Brisbane Roar stalwart's third Julie Dolan Medal, though it isn't expected.

Kerr's Glory finished as runners-up to Sydney FC, who boast a string of possible stars and potential winners.

Equally, premiers Melbourne Victory boast two potential winners in midfield maestro Christine Nairn and Natasha Dowie.

Unlike the A-League prize, no foreign woman has ever claimed the Julie Dolan Medal.

Nathan Burns (in 2014-15) is the sole Australian to have won the Johnny Warren Medal in the past decade, with star imports again expected to fight for the accolade.

Perth Glory's Diego Castro, Sydney FC's Milos Ninkovic -- both former winners -- Wellington forward Roy Krishna or long-serving Adelaide midfielder Isaias are the leading chances.

Krishna, who scored 18 goals in 25 A-League appearances this season, will receive his prize as the A-League golden boot winner.

The Johnny Warren Medal, named after the much-loved former Socceroos captain, is voted on by officials, past players, media and technical experts.

Adrian Mierzejewski claimed last year's prize.

Awards for goalkeeper, coach, referee and young footballer of the year in both the A-League and W-League will also be announced.