Steven Pressley got off to a bad start on his Dens dugout debut and now needs a win on the road at Alloa Athletic to stop Dundee's League Cup dreams from going up in smoke.
Fans were far impressed when former Dundee United skipper Pressley was handed the reins in the summer, given his less than stellar record as a manager south of the border with the likes of Coventry, Fleetwood Town and Carlisle.
He needed to start well to get the punters onside but Dundee were instead booed off after losing 1-0 at home to an Airdrie team who would have been relegated to League One last term had Hamilton not been hit with a massive points deduction.
We thought the Diamonds looked a good price to spring a shock at 13/2 in Saturday's football tips but unfortunately picked out a goals bet for our Super Single that backfired as Pressley's side drew a blank.
The Dark Blues can ill afford any more slip-ups if they want to progress from Group C and now take on an Alloa side who have already banked six points from their first two games.
The League One Wasps have already seen off Bonnyrigg and Montrose so they will be confident of stinging Dundee and piling on the pain for Pressley.
How the bookies view it: Dark Blues to bounce back
Despite flopping last weekend, Dundee are still odds-on favourites for this one at 2/5 with BoyleSports. Alloa are 9/2 outsiders and the draw pays 7/2.
Head to head: Dundee bossing it
Dundee have dominated this fixture, winning 18 of the 26 meetings and losing just four. They last met five seasons ago in the Championship, with the Dark Blues winning two of the three meetings and the other game ending in a draw.
Players to watch: Garza's a goal threat
Cesar Garza was brought in on loan by Dundee from Mexican club Monterrey last term and had a few attempts on goal in the loss to Airdrieonians. He should offer a threat again in this cup tie, although the bookies are unlikely to offer any scorer prices again.
Stefan Scougall is another midfielder with an eye for goal and he chipped in with seven goals last term for Alloa. The 32-year-old will fancy his chances against a Dundee defence that looked a little vulnerable last weekend.
Probable line-ups
Dundee don't have any injury issues but Pressley may freshen things up a bit after a disappointing display last time out. Alloa were in action on Tuesday night so boss Andy Graham may also make a few changes.
Alloa Athletic: McFarlane, Taggart, Waters, McKay, Devine, Scougall, O'Donnell, Rankin, Orsi, Sammon, Buchanan.
Dundee: Carson, Samuels, Astley, Koumetio, Graham, Digb, F Robertson, Yogane, Wright, Garza, Murray.
Anything else catch the eye?
Recreation Park has been a happy hunting ground for Dundee, with the Dark Blues scoring three times on each of their last four visits. Based on their display against Airdrie, that run is unlikely to continue in this cup tie.
Backing a narrow win for Pressley's side looks the best option and combining a Dundee win with under 3.5 goals pays 11/8 at BoyleSports.
That weekend jolt should give Dundee added motivation for this one though and backing them to be winning at half-time and full-time could also pay off at 23/20.
Both games involving these sides ended in 1-0 scorelines last weekend so there could also be some value in going for under 2.5 match goals at 13/10.
GambleAware