Wollongong United's Robbie Shields and Dapto Dandaloo's Sam Munro will go toe-to-toe on Friday evening in a bid to be named the 2014 season's George Naylor Medallist.
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Shields is vying to become the first player since the award was introduced in its current format to win in successive seasons, while Munro will be aiming to end a series of runner-up finishes.
The award is given on a points basis to the Illawarra Premier League's most valuable player during the regular season.
A 27-goal haul from Shields has the former Leeds United junior in a strong position to win his second successive medal.
The last person to win back-to-back was Matthew Horsley in 1989-1990.
"It is a massive achievement just to nominated again and it would be an unbelievable achievement to win it," Shields said.
"I am happy to be in the same category as Sammy. It is a big honour especially as this season didn't go quite well as a team performance.
"We were happy enough to win the Bampton Cup [but] it is an achievement definitely."
Shields set a target at the beginning of the campaign to score more goals and his ability to execute has no doubt been a major factor in his bid to go back-to-back.
"You can only score goals with the players around you. The boys have been brilliant this year," he said.
"The chances they have created for me have been fantastic."
Meanwhile, Munro will be looking to make it third time lucky after finishing the bridesmaid in 2011 and 2012.
The Fury midfielder is hoping to add to his trophy cabinet after Dapto-Dandaloo claimed the grand final against Bulli a month ago.
"Obviously you are playing a team sport so first thing first, you want to win the team trophies but these individual awards are always great to get at the end of the year. Just to be up there is a good thing," Munro said.
"It would be massive [to win it]. I really respect this league."
"It is a big league. I have played up in Sydney in the NSW Premier League and in the A-League Youth League, and this Illawarra league is a very serious competition.
"All the teams are quite competitive, so it would be a great honour for me to win this trophy."
The Neville Arrowsmith Medal for District League player of the year will be between Jason Rea (Corrimal Rangers) and Nathan Mucci (Helensburgh Thistle).