There are not too many more daunting games with which to start life in charge of Pompey.
Simon Bassey takes the team to Premier League giants Tottenham this weekend in the third round of the Emirates FA Cup.
The Londoners moved into their impressive new home – with a capacity of more than 60,000 – in 2019.
And with a fleet of coaches transporting Blues fans up from the south coast, Bassey hopes they will have a day to remember.
The interim head coach said: “I went to the opening game at the stadium and it’s a fantastic arena – one of the best in the world.
“It’s a great honour to come up against a manager of Antonio Conte’s pedigree. We watched the game against Crystal Palace earlier in the week and they found their form in the second half.
“The challenge is brilliant one and it’s something we’re all looking forward to. It’s not often that Pompey are underdogs, but we will be on Saturday.
“We take a great following wherever we go and to sell around 9,000 tickets as quickly as we did is fantastic. Hopefully we’ll give them something to shout about.
“It’s a good group here in a difficult moment and we’ll look to give a positive account of ourselves to show there’s some fight left in us.
“We have to be sensible. In my previous jobs we’ve come up against West Ham, Liverpool and Spurs at Wembley.
"It’s a good group here in a difficult moment and we’ll look to give a positive account of ourselves to show there’s some fight left in us."
“It’s about being in the game and not doing anything stupid. We’ve got a good plan, but they’ve got world class players and we’ll have to be right at our limit.”
There are a few players in the treatment room and midfielder Marlon Pack is suspended, but Pompey could welcome back one long-term absentee.
Bassey said: “We’ve got a few injuries and picked up another one this week, which is unfortunate, but Louis Thompson is back in the group and that’s huge for us.
“He’s a fantastic player and is also brilliant around the changing room, so he’s a great person to have in the squad. There’s never a quiet moment when he’s about.
“Clark Robertson is still undergoing treatment and it’s probably too soon for him, while we don’t envisage any of the others being back in the next 10 days.
“There are nine subs on Saturday, so we’ll bring some academy boys into the group and that will be a great experience for them.”
Bassey will be assisted by lead professional development phase coach Zesh Rehman following the departure of Danny and Nicky Cowley on Monday.
He said: “This part of football is never nice and it’s been a sad week for everyone – especially when it’s two people as honest and hard-working as them.
“I’d like to thank them for bringing me here and all the support they’ve shown along the journey. I’m pretty sure they’ll be back in football soon.
“It helps to have some continuity in the short-term and Zesh is a really good guy, who we’ve worked closely with this season.
“He gives a fresh pair of eyes to the staff and can offer a different insight. It’s always nice to get that extra opinion.”