It's 115 years since Dundee last lifted the Scottish Cup…and the layers reckon the wait will continue when they visit Tynecastle on Friday night.
The first of the quarter finals should be a cracker and both will view it as a decent chance of reaching the last four.
However, Dundee have arguably bigger fish to fry and they are in a survival fight for their Premiership future after a horror recent run.
They haven't won a league since five days into 2025 and they are in freefall. However, they've managed to eliminate neighbours Dundee United from the Scottish Cup and also demolished Championship Airdrie.
But they must still have flashbacks to one of those recent league defeats – Hearts visited Dens Park and crushed them 6-0 just over a month ago.
Hearts will be on a real downer too after another derby defeat to Hibs at Easter Road last week. That's put the spotlight and pressure back on manager Neil Critchley again.
They scraped through the last round after a late equaliser at St Mirren before they won a penalty shootout. Previously to that Hibs loss though, they won agaianst St Johnstone and St Mirren.
How the bookies view it: Strong confidence in Hearts
Hearts are very short across the board at 4/7 with Boylesports. Dundee can be backed at 4/1 with the same firm and the draw is 11/4.
Recent head to heads: Dundee hit for six
As stated. Hearts ran amok on their last visit to Dens Park and romped to an incredible 6-0 win. Hearts also won 2-0 at Tynecastle in December.
The hosts ahve won the last three meteings in Edinburgh with Dundee's last win coming in 2022.
Players to watch: Murray magic
Simon Murray has pretty much carried Dundee all season and bagged his 17th goal of an excellent campaign last week against St Johnstone. The former Hibs striker looks excellent value to score anytime at 7/2 with bet365.
Elton Kabangu has been in fine form for Hearts since his loan move from Belgian football. He netted a double at Dens Park on his last visit and is 15/8 to score anytime with bet365.
Predicted line-ups:
Hearts are expected to be without the injured Cammy Devlin, Yan Dhanda, Craig Halkett, Frankie Kent and Stephen Kingsley.
Dundee have doubts over Seb Palmer-Houlden, Antonio Portales, Clark Robertson, Billy Koumetio and Scott Fraser.
Hearts: Gordon, Drammeh, Steinwender, McCart, Penrice, Baningime, Grant, Spittal, Shankland, Wilson, Kabangu.
Dundee: Carson, Mulligan, McGhee, Shaughnessy, Donnelly, Larkeche, Sylla, Garza, Cameron, Adewumi, Murray.
Anything else catch the eye?
Hearts look way too short here in what could be a close game….despite their romp here last month.
Dundee have tightened up with the return of captain Joe Shaughnessy and there's next to no chance Hearts will have it as easy…even at Tynecastle.
The call here is to back Dundee on the double chance of a draw or a win at 5/4 with Boylesports. The pressure of relegation is off them and Hearts could find their fans on their back after last week's disappointment.
Since that game in February, all Hearts' game s have seen both teams scoring and it's the same with Dundee's last four matches too.
Back both teams to score and over 2.5 goals at 7/5 with Boylesports.
This Scottish Cup match between Hearts and Dundee will be played on and kick off at 19:45. Check below for our tipsters best Hearts vs Dundee prediction. You may also visit our dedicated betting previews section for the most up to date previews.
