On Tuesday, Scottish Premiership side Dundee will play host to third-tier Annan Athletic in a Scottish League Cup clash.
Having claimed consecutive victories, Dundee are sitting in second place in Group D and just one point adrift of Annan, who have played a game more.
Match preview
Dundee are currently looking forward to their second consecutive top-flight campaign after Tony Docherty led the club to an impressive sixth-placed finish last season.
Docherty was subsequently rewarded with a contract extension, ensuring that he will remain at Dens Park for the 2024-25 campaign.
The Dundee boss saw his side begin their Scottish League Cup group with a resounding 7-1 away victory over fourth-tier outfit Bonnyrigg Rose.
They claimed another away victory last Tuesday, with Luke McCowan and Ethan Ingram scoring second-half goals to condemn Arbroath to a 2-0 defeat.
The Dee are now looking forward to their first home match of the new season, and they will be desperate to claim three more points after failing to win any of their final five home matches of the 2023-24 campaign.
Annan are preparing for a second consecutive season in the third tier after they collected 39 points from 36 matches to finish outside the bottom two on goal difference.
After avoiding an immediate return to League Two, Annan are now hoping to improve under the watch of player-manager Willie Gibson.
The Annan boss began his tenure with a narrow 1-0 victory against Inverness Caledonian Thistle, before they were held to an underwhelming 2-2 draw against Bonnyrigg Rose, with their opponents winning the subsequent shootout to take home the bonus point.
They quickly returned to winning ways in Saturday's away clash with Arbroath, as Tommy Goss, Josh Dixon and Josh Todd all got on the scoresheet to secure their side a commanding 3-0 victory.
Annan will now turn their focus to their first meeting with Dundee since October 2009, knowing that a surprise win would be enough to seal top spot and progression to the knockout rounds.
Team News
Dundee's Docherty could be tempted to stick with the back three of Juan Portales, Ryan Astley and Jordan McGhee.
Simon Murray, who returned to the club earlier this month, is in contention for a starting place after making his second debut as a substitute in the win over Arbroath.
Murray could operate in a front-two pairing with Curtis Main, who scored his first career hat-trick in the 7-1 demolition of Bonnyrigg Rose in the first group game.
Meanwhile, Annan will have to assess Aidan Smith's fitness after the forward was forced to miss the 3-0 win over Arbroath.
Paul McGowan was also absent from Saturday's squad, but there is hope that he can recover from illness in time for the midweek away contest.
Hibernian loanee Malik Zaid is expected to retain his place after he made his Annan debut at the weekend.
Dundee possible starting lineup:
McCracken; Portales, Astley, McGhee; Ingram, Cameron, McGowan, Sylla, Robertson; Murray, Main
Annan Athletic possible starting lineup:
Smith; R Muir, T Muir, Kilsby, Quitongo; Smith, Dixon; Zaid, McGowan, Todd; Goss
We say: Dundee 2-0 Annan Athletic
Having recorded back-to-back victories, Dundee will carry significant momentum into Tuesday's fixture, and we think tht they will showcase their extra quality to claim a relatively comfortable victory over their third-tier opponents.
For data analysis of the most likely results, scorelines and more for this match please click here.
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