This month, new Dundee manager Gary Bowyer will get an early taster of what life in the Championship is all about.
The 51-year-old has had plenty of experience in English football but Saturday’s Premier Sports Cup opener will be his first flavour of competitive Scottish football.
Embracing the new challenge has been his mentality since his unveiling a month ago.
And, though they are top seeds in their League Cup group, it will be a challenge for the Dark Blues.
That’s because Group H is the most Championship-heavy section in the entire competition with a trio of second-tier outfits jostling for a place in the knockout stage.
So what will Dundee need to be ready for?
Hamilton Academical (h) – July 9
Accies have not pulled up any trees since they themselves were relegated from the top flight a year ago.
In their first season back in the Championship last term, they rarely troubled the play-off places.
Now, though, there is a new man in charge in former Dundee United and Hibs man John Rankin.
Their squad is small but boasts a couple of former Dees in the shape of club captain Brian Easton and battling midfielder Lewis Spence.
With the likes of Spence, Scott Martin and Miko Virtanen in midfield Accies won’t be short of bite in the middle of the park.
Last meeting: Dundee 0-1 Hamilton (Andreu) – May 4, 2019
Overall record: W79 D35 L41
Stranraer (a) – July 16
Jamie Hamill’s first season as manager saw Stranraer finish five points short of the promotion play-offs in League Two.
They finished the season strongly, winning three of the last four and have been busy in the summer transfer market.
Six have come in, including Scott Dunn from Queen of the South, Sam Ellis from St Mirren and George O’Connor from Kilmarnock while 13 have departed.
As well as Hamill, the Blues have another well-kent face in the shape of 38-year-old striker Darryl Duffy, formerly of Rangers, Falkirk and Hull City. He is also the club’s assistant manager.
Last meeting: Dundee 5-0 Stranraer (Higgins, Harkins, McMenamin (2), Griffiths) – August 1, 2009
Overall record: W12 D3 L1
Queen’s Park (a) – July 19
The ambitious Spiders are preparing for their first season in the second tier in 40 years.
Experienced manager Owen Coyle will be in the dugout, fresh from success in India with Jamshedpur and Greg Stewart.
Their attack will be spearheaded by a resurgent former Dee in the shape of Simon Murray.
He signed a new deal over the summer after playing a key role in their promotion through the play-offs, taking Dunfermline’s place in the Championship.
Joining Murray at the club have been tricky winger Dom Thomas from the Pars, full-back Jason Naismith from Kilmarnock and Grant Savoury from Peterhead as they look to make a mark this season.
At the other end of the park, ex-Dundee goalie Calum Ferrie was first-choice keeper last season and has taken the No 1 jersey for the upcoming campaign.
Last meeting: Queen’s Park 2-1 Dundee (Longworth, Burns; Milne) – August 29, 2012
Overall record: W54 D12 L17
Forfar Athletic (h) – July 23
The Loons must be fed up of the sight of Dundee, having drawn them at this stage of the competition in each of the past three seasons.
Gary Irvine returned to Dens Park with his Forfar side a year ago but were beaten 5-2 and will be hoping for a closer contest this time around.
The Angus side had a good season last term, finishing up as the best-of-the-rest behind runaway league winners Kelty Hearts but losing out in the play-offs.
Former Dee Jamie Ness has retired due to injury but Callum Moore remains at Station Park while Irvine has added former United man James Keatings to his strikeforce.
Last meeting: Dundee 5-2 Forfar Athletic (Adam, Panter, Elliott, Cummings (2); McCluskey, Anderson) – July 24, 2021
Overall record: W15 D1 L2