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The Irish started the group in poor fashion after two opening defeats and now face a daunting trip to Cristiano Ronaldo and co.
On the face of it, the Republic of Ireland could be in for an extremely tricky evening, but there will be little temptation in backing Portugal to win at a short price of 1/5.
Ahead of the game, our tipster Robert Mann takes a look at some of the best bets from Portugal vs the Republic of Ireland to get your teeth stuck into.
Portugal are 1/5 to win, with the Republic of Ireland priced at 16/1 to come away with the victory. A draw is priced at 5/1.
Prediction: 3-0 (5/1)
Half-Time/Full-Time: Draw/Portugal (5/2)
Given the attacking talent in the Portugal squad, expansive football has been demanded of head coach Fernando Santo for some time now.
And considering that the Republic of Ireland haven't won any of their last 13 competitive matches - only scoring five times in that run - we're backing the Portuguese to lead from the first to last whistle on Wednesday night.
First Goalscorer: Cristiano Ronaldo (6/4)
Barring their 1-0 defeat to Belgium in the European Championships, Portugal have been involved in some high-scoring affairs.
Win to Nil: Portugal (8/11)
Republic of Ireland last played Portugal in a 5-1 defeat back in 2014 - and we’re backing a similar outcome on Wednesday evening.
While the Portuguese are winless in their last three matches, it has been against very strong opponents - a label that can’t be said for Kenny’s men.
Odds are correct at the time of publication and are, as always, subject to change. Please gamble responsibly. For more information visit: https://www.begambleaware.org.
Ricardo Pereira's long road back to international football looks set to continue a little while longer following his hamstring injury at the weekend, while Ronaldo will have his sights on a record-breaking 110th international goal.
The Republic of Ireland have welcome uncapped defenders Nathan Collins and Andrew Omobamidele to the group for the first time, but will be without experienced midfielders James McCarthy and Robbie Brady.