East Fife start their near 400-mile round trip journey to Brora Rangers at 11am and Gary Naysmith’s side are still sore at the loss of a last minute goal that saw them go down 3-2 to Berwick Rangers on Saturday.
The Fifers had battled back from two goals down to level in the second half, but lost out to a last-minute goal.
The Bayview boss said: “This is a long journey to face a strong side full of experienced players and we wanted to be doing it with a positive result behind us. It was not to be, despite a bit of a rally in the second half.”
Naysmith’s men started the season with a win over Forfar in the First Round of the Petrofac Training Cup and a brave display at Stranraer in the Scottish League Cup saw them go down 1-0 to a last-minute goal.
Since then two defeats in League Two have knocked progress, but Naysmith is convinced that his men will turn the corner.
He said: “We have lost to Arbroath and Berwick but we are not far away from getting things right.
“I am conscious that we have not had a great start but we will improve. We have players with ability.
“However, there is work to be done to create a winning mentality. This game will be a test of character for everyone and I want us to be coming home with a win over Brora.”
Kevin Smith returns from a ban, but back-up goalkeeper Dylan Rooney is a doubt and Cyrus Moosavi remains out long term.
Brora Rangers will look to match Highland League rivals Formartine United’s march to the quarter-final stages of the Petrofac Training Cup last season by winning at their Dudgeon Park home.
The Highland League champions’ squad contains former Inverness Caley Thistle defenders Grant Munro and Ross Tokely.
Brora warmed up for their meeting with Fife with two 8-0 wins in a row over Halkirk United and then Turriff United.
Manager David Kirkwood, who had a spell at East Fife as a player, said: “We worked really hard to get through in the last round against Stenhousemuir and we will need to do the same again against East Fife.
“They have had a couple of disappointing results in the league. They have a decent squad and defeated Forfar in the first round of this competition. We will need to play really well to get into the last eight.”