Pressley's Coventry City travel to the Emirates to take on Arsene Wenger and Arsenal in an FA Cup fourth-round tie that will be beamed live on television and has the 40-year-old Scot trying to keep his excitement in check.
By his own admission, Pressley has had a dramatic 11 months at Coventry. Despite a 10-point deduction imposed by the Football League for being in administration, his team have romped up the Sky Bet League 1 table, and are currently 11th of the 24 teams; they would be in a play-off spot but for the points deduction. As wrangles continue over the club's rights to the Ricoh Arena, Coventry also play each home game 35 miles away, at the Sixfields Stadium in Northampton.
This cup tie against Arsenal, however, is one of those games that will be a defining chapter in Pressley's career to date. "It is the most prestigious game I have ever been involved in," he says. "Maybe not the most significant, in terms of the outcome - the league remains our priority - but it is certainly my biggest game in terms of the opposition, the manager, and the stadium.
"I know full well what I will be up against: a team full of world-class players, led by a world-class manager. But we will go to the Emirates and believe that we can do something. We will go there, in fact, and try to impose our own philosophy on Arsenal."
Pressley, to the annoyance of some, is bullish in his self-belief, and it appears to work. He has reinvented Coventry with youngsters galore, and with his former Hearts team-mate, Andy Webster, a near-veteran in his defence. Pressley's players, on all available evidence, appear to take his rampant convictions out on to the pitch with them.
"I'm being genuine when I say we will try to impose ourselves on Arsenal," he says. "We can't really deviate from our style. We won't go to contain, to sit in. My players play a high-intensity, high-pressing, highly-aggressive type of football - by aggressive I mean in their pursuit of the ball, with constant pressing and quick passing. That is our philosophy, our DNA as a team now, and we will try to apply that against Arsenal. Our bravery in possession will be key. It is a part of our game as a team and we must apply the same principles against Arsenal. If not, then we will have no chance; it will be one-way traffic. I've no doubts we can perform well in the Emirates. No doubts at all about that. And remember, I've got previous."
Yes, Mr Pressley, you do. Back in September, 2011, then in charge of Falkirk, he guided that club to a memorable 3-2 win over Ally McCoist's Rangers in the League Cup quarter-finals. Pressley believes that memory can spur him on when facing Wenger.
"I've been here before, facing a gulf in standards, so I know it can be done. Back then I managed a Falkirk team full of 17-year-olds and 18-year-olds to that cup win against Rangers - a Rangers team, by the way, that had not lost a domestic game so far that season. We managed to get a remarkable performance and a remarkable result that night, so I know it can be done. It is perfectly possible."
Pressley claims to have his Coventry team coached and prepared in such a way that there is a precision about their football, whereby any mistake in the system can be traced within seconds to a specific player. "We're well primed," he says. "We've got that philosophy about the team now, where everyone knows exactly their job on the pitch. Every plan, every tactic, can be pinpointed. So that helps us a lot.
"Listen, I'm not naïve. I know of the might of Arsenal. They will have to be below par and we will have to be at the top of our game to get anything. But we will have a clear game-plan in London."
Pressley goes to the Emirates with pressing problems. His main goalscorer, Callum Wilson, is out injured while his sought-after striker, Leon Clarke, has handed in a transfer request.
Yet one player, Pressley asserts, continues to shine for him: the former Rangers midfielder John Fleck. "He has been outstanding this season, a revelation," said Pressley. "The Emirates, I believe, will be a great stage for John. There is a bit of old-school in me, and there is something about John's style I really like.
"He has a street-football side to him: he plays his football just like he would if he had taken his jacket off down the public park.
"He has a real game-intelligence, a real reading and appreciation of a match situation. He's also fitter than he's ever been and has answered questions about whether he could play the kind of high-intensity football I want my team to play. John knows exactly what I and the team require of him. He's been brilliant, and he won't be intimidated one bit by Arsenal." Pressley is trying to rebuild despite the political wrangles engulfing the club. The supporters have certainly taken to him.
"Our fans have been incredible. We took 7000 with us recently to MK Dons and the atmosphere was electric. We have older fans at Coventry who remember the Premiership years, so being in League 1 is pretty painful for them. But we also have a new generation of supporters, and what I'm trying to do is create a fine team and some good memories for them."