A year on from thrilling the nation by reaching the World Cup final four, the Three Lions have another shot at glory after reaching the competition's inaugural finals in Portugal.
England are just two wins away from the senior side's first major trophy since the 1966 World Cup, but preparations for the competition have been disrupted by the unprecedented all-English Europa League and Champions League finals.
Seven of Southgate's selection were involved in Saturday's clash between Liverpool and Tottenham, giving the Three Lions staff precious little time to prepare to take on Holland in Guimaraes.
"Well, it's been a strange, different sort of preparation," the England boss said.
"But every time you get together with international teams, there is always complications of some sort.
"In March, we lost eight players with injury and young players came in and played brilliantly, so we've shown incredible adaptability and resilience as a team over the last two years in particular.
"I think in terms of where the players are at, I have got to assess all the players that were involved in Madrid because it's a unique game, a unique set of circumstances, whether you won or lost.
"The emotion of it, the physical implications, the fact that the players only arrived on Tuesday and there's a lot of tactical work that has been going on, so I've got to assess them all."
Liverpool captain Jordan Henderson is the only doubt for the semi-final at the Estadio D. Afonso Henriques, although Kane's availability is a big talking point.
Quiet in Spurs' Champions League final loss after a seven-week absence with an ankle injury, Southgate says the striker is fit to start against the Dutch.
"I was at the game, I wanted to see the game," the England manager said.
"We have our own observations on how that game played out. The only thing I would say was that a lot of the service that went into Harry, he wasn't favourite when it was arriving with him or in his area."
With Kane potentially dropped to the bench, there has been talk that Raheem Sterling will captain his country for the first time on the night that he wins his 50th cap.
A PR firm associated with the England forward suggested he was set to skipper the side - something that left the player "fuming" and Southgate tight-lipped.
"If I confirm anything about the team other than that Raheem is playing then I'm doing half of Ronald (Koeman's) job for him, so I don't want to discuss the captaincy," he said.
"Basically Harry Kane is our captain. If Harry Kane doesn't play, then I have a decision to make."
The England line-up might be uncertain but the determination to cap progress with silverware is clear.
"We know, of course, in the batting order that it's the World Cup, European Championship," Southgate added.
"We now have a new competition, which only the best 12 teams in Europe could enter in our division.
"We're through by right through a really difficult group, as are the other teams in it. So, we want to be in the habit of starting to win things.
"Last summer we didn't have a free hit at the World Cup because when you play for England there's no free hit at anything, but there was less expectation.
"But we weren't as far progressed as a team. Now I feel that we've gained confidence from getting to the semi-finals.
"We didn't want that to be the end of it. We felt that we have got the players who are capable and hungry to go on and to start to win things.
"We always want to be in the latter stages of tournaments, where the big games are the opportunity to win trophies. That's what this competition provides over the next few days."
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