The Tartan Army were looking for a response following a 4-0 defeat by the Netherlands in Amsterdam on Friday night but were shocked when midfielder Conor Bradley fired in for the visitors after 32 minutes.
The home side picked up the pace after the break but could not break down Michael O’Neill’s determined side, who stood firm to register Northern Ireland’s first win in Mount Florida in almost 50 years.
Scotland have not been on a seven-game winless run since August 2004 to March 2005 and they take on Gibraltar and Finland in June friendlies before they face hosts Germany in the Euro 2024 opener at the Allianz Arena.
Somehow they need to regain their groove or there could be more pain to come.
The Scots had long since booked their place in this summer’s Euros with a terrific qualifying campaign but they were under a bit of pressure following the Dutch defeat.
Manager Steve Clarke made two changes with centre-back Liam Cooper in for Ryan Porteous and striker Lyndon Dykes in for Lawrence Shankland.
There was a youthful look about O’Neill’s side which showed three changes from the team that started in the 1-1 draw in Romania, with former St Johnstone midfielder Ali McCann, Dan Ballard and goalkeeper Bailey Peacock-Farrell returning at the expense of ex-Celtic stopper Conor Hazard, Jordan Thompson and Paddy Lane.
Scotland tried to build some early pressure after midfielder Ryan Christie curled an effort from the edge of the visitors’ area wide of the post, but Northern Ireland were not unduly bothered.
The game drifted along with Peacock-Farrell having next to nothing to do before it took an unexpected turn.
Scotland wing-back Nathan Patterson recovered well to rescue an original mistake when a pass deep inside his own box was intercepted by Bradley and the 20-year-old Liverpool defender turned inside before firing high past goalkeeper Angus Gunn, with the aid of a slight deflection off defender Jack Hendry for his first international goal.
Then Scotland captain Andrew Robertson went off with an injury to be replaced by midfielder Lewis Ferguson and the home side returned to a back four with Kieran Tierney moving to left-back.
Northern Ireland almost doubled their lead on a speedy counter, with Shea Charles guiding the ball just wide, as did Scotland midfielder Scott McTominay – moments later – at the other end.
Boos from the home fans accompanied the half-time whistle.
Scotland started the second half with increased tempo but there still remained a lack of incision and guile and while Jamie Reid fired wide to end a Northern Ireland attack, at least it was an effort on goal.
In the 63rd minute, John McGinn’s free-kick came off Liam Cooper’s shoulder and skipped past the visitors’ goal and the home fans drove their side forward with increasing gusto.
Tierney was finding space down the left but the Scots could not capitalise.
Che Adams and Kenny McLean replaced Dykes and Gilmour in the 68th minute before Shankland and Stuart Armstrong also came on for Christie and McGinn.
Shankland soon had a close-range shot blocked by Brodie Spencer and Peacock-Farrell tipped a Ferguson header over the crossbar for a corner, before Shankland sent a header over and then four added minutes ran out.
Scotland have regressed recently in terms of results but it is this performance that should primarily concern Clarke.
Memphis Depay's 89th-minute free-kick made sure the Netherlands avoided defeat in the friendly fixture between two nations preparing for Euro 2020.
The influential forward had also scored in the first half, his left-footed volley cancelling out Jack Hendry's opener for a Scotland team left shorthanded following a positive coronavirus case within the squad.
Substitute Kevin Nisbet restored Scotland's lead soon after coming on as the Dutch looked defensively shaky when lining up in a wing-back formation, though De Boer made clear the squad had little time to work on systems ahead of the match in Faro.
"Has the experiment with the 5-3-2 system failed? No, it has not," De Boer said in his post-match interview with broadcasters NOS.
"I'm not worried at all. We only trained on it once, only three times for 10 minutes. In addition, we also played 4-3-3 at the time.
"In addition, Georginio Wijnaldum and Frenkie de Jong only joined later.
"It seems clear that things need to get better. I saw a few good moments, but there were too few."
Scotland qualified for their second consecutive European championships after a strong qualifying campaign saw them finish second in their group behind Spain.
In Euro 2020, Scotland were knocked out at the end of the group stage having earned just one point from their three games.
Now, Robertson has urged the Tartan Army to become the first side in the nation's history to make the knockout stages of the competition, despite the tough test ahead of them.
"We know that's what's at stake," said Robertson in a press conference. "We've got a lot of incentives, but one is becoming that legendary squad - that has to drive us forward.
"We have to be at our best and if we can do that, who knows where we'll be come 23 June.
"We don't want to have any regrets this time. What's the worst that can happen? We go on to a long list of teams that haven't made it out the group, or we put ourselves in a position to make history.
"We're excited by the challenge, we're excited about what's ahead, and if we perform the way I know we can perform, then I'm confident we can make history."
Steve Clarke is the first Scotland manager to lead the team out in two consecutive Euros, and he is confident his team can block out the noise surrounding the fixture and get a positive result.
"One of the mantras I've had is respect everyone and fear no-one," Clarke said. "We know they're a good team, but hopefully, we can show everyone we're a good team as well.
"We're proud we've been able to do back-to-back tournaments and hopefully, by the end of this, we'll be even more proud at having done something a bit more special."
Steve Clarke’s side started well in the first half of the friendly at the Johan Cruijff Arena in Amsterdam until the Dutch took the lead against the run of play five minutes from the break with a powerful Tijjani Reijnders drive.
Scotland striker Lawrence Shankland missed a glorious chance in the 62nd minute when he was through against Dutch goalkeeper Mark Flekken with the Hearts captain clipping the crossbar with his shot.
It started to go really downwards for the Scots 10 minutes later when Georginio Wijnaldum headed in a second before substitutes Wout Weghorst and Donyell Malen added late goals.
Scotland have gone six games without a win for the first time since a run from October 2007 to September 2008 and ahead of the friendly against Northern Ireland at Hampden Park on Tuesday, Watford defender Porteous conceded improvement was required.
He said: “It was disappointing. We were more than in it for long spells.
“We had a number of good chances to get ourselves on level terms or maybe even go in front but ultimately the goals we have conceded have stopped us getting anything from the game.
“It is going to be hard to focus on the positives because of the manner of the result.
“But even if we’re getting beaten in games we can’t concede the goals that we have done. That can’t happen.
“We’ll definitely take a look at them. But up until the 65th minute we’re more than in the game but the sloppy goals and things that we can do better has cost us.
“It’s tough when you’re playing against these teams but we’ve shown that we can do it.
“We are going through a spell right now with six games, we’ve conceded a number of goals and it’s definitely something we want to rectify as a team and, lucky for us, we’ve got another game on Tuesday to try to do that.”
The match, which serves as a first preparation game for the European Championship in the summer, may well have turned out differently had Shankland netted when he was through against Flekken, but former Hibs defender Porteous was understanding.
He said: “I thought he was excellent against arguably the best centre-half in the world (Virgil van Dijk).
“His game has come on leaps and bounds in the last year and he can hold his head up high after that performance.”
Scotland suffered the heaviest defeat in an opening game at any European Championship on Friday, being routed 5-1 by a rampant Germany team in Munich.
Florian Wirtz, Jamal Musiala, Kai Havertz, Niclas Fullkrug and Emre Can all scored for the hosts, while Ryan Porteous was sent off for a horror challenge on Ilkay Gundogan.
It was the first time Scotland had conceded five or more goals in a game since a 5-1 friendly defeat to the United States in 2012, and the first time in a competitive match since a 6-0 loss to the Netherlands in Euro 2004 qualifying 21 years ago.
At the other end, meanwhile, Scotland failed to record a shot on target in a major tournament game for the first time since Euro 1992 (0-1 versus Netherlands).
Asked what he had done in response to the defeat, Clarke said on Sunday: "Kick a couple of backsides, give some cuddles, make the players understand why the Germany result happened and make sure it doesn't happen again.
"I've spoken to one or two players around the squad whose opinion I value. I had a good chat with a few of them.
"I think their interpretation of what we asked them to do was wrong, so we've worked on that."
Scotland must now pick themselves up for Wednesday's meeting with Switzerland, who began their own Group A campaign with an impressive 3-1 win over Hungary.
The Tartan Army could lose their first two matches at a tournament (World Cup/Euros) for the fourth time, having done so at the 1954 and 1986 World Cups and Euro 1992.
However, Clarke insists confidence in the camp is still high, adding: "We believe in ourselves, there's no danger of that. We know it was a bad night.
"We have to accept all the criticism that comes our way and then we have to put it right. To be in football, you have to be very resilient."
The visitors controlled much of the first half and hit the goal frame through Ryan Christie but the Dutch took the lead five minutes from the break with a Tijjani Reijnders thunderbolt.
Scotland continued to create and miss chances in the Johan Cruijff ArenA – as did the Netherlands – before Scotland striker Lawrence Shankland hit the bar in the 62nd minute with only Dutch goalkeeper Mark Flekken to beat.
It was a glorious chance for Scotland and they were made to pay 10 minutes later when Georginio Wijnaldum headed in a second and then goals from substitutes Wout Weghorst and Donyell Malen in the 84th and 86th minutes turned a good performance on its head as Clarke now looks to get back on track against Northern Ireland at Hampden Park on Tuesday night.
Many of the Tartan Army had clamoured for in-form Hearts striker Shankland to be handed a start and he will know he should have scored to cap off a good performance.
Keeper Angus Gunn was back after injury along with several familiar faces such as captain Andrew Robertson and Kieran Tierney, with the visitors backed by around 2,400 travelling fans.
Ronald Koeman’s side had a mixture of youth and experience but included top names such as captain Virgil Van Dijk and another former Celtic defender, Jeremie Frimpong, with Memphis Depay leading the line.
But the Scots started with confidence, Shankland’s touches were assured, full-back Nathan Patterson stretched the Dutch down the right-hand side with Robertson working the left flank.
However, there was danger when Cody Gakpo went clean through on the Scotland goal but he failed to finish and was eventually flagged offside.
After midfielder Scott McTominay was booked after just nine minutes for fouling Xavi Simons, Shankland headed a Patterson cross over the bar.
Then, in the 18th minute, midfielder Billy Gilmour raced down the right and his cross was met by the head of Christie but Netherlands keeper Flekken tipped the ball on to the bar and it did not fall kindly for Shankland.
Gakpo’s blatant dive inside the Scotland penalty area did not fool Belgian referee Erik Lambrechts and moment later at the other end McGinn flicked a Christie cross over the bar.
However, the Scots walked into a sucker punch just before the break when AC Milan midfielder Reijnders took a pass from Gakpo and, with little pressure on him, measured his shot from 25 yards and arrowed it high past the helpless Gunn.
McTominay had a shot blocked by Reijnders inside the Netherlands box at the start of the second half but Gunn had to make a great save from Depay’s shot on the turn.
More excitement followed at both ends.
McGinn’s shot was parried by Flekken before Christie headed a cross from the Villa player past a post and then Gunn saved from Gakpo’s 20-yard drive.
When Shankland found himself through against Flekken with the goal beckoning, his shot clipped the bar on the way over and he was soon replaced by Che Adams, with John Souttar and Lewis Ferguson also coming on.
However, the Netherlands doubled their lead with a simple goal, Gakpo’s cross being headed in by Wijnaldum from eight yards out.
McTominay headed a cross from substitute Anthony Ralston over the bar to continue the theme of missed chances before Scotland folded as Weghorst headed in a corner and fellow substitute Malen ran through to grab a fourth – and the damage could have been greater.
Kevin Csoboth scored the winning goal in the 10th minute of injury-time to put Scotland out of another major tournament in the group stages.
However, things could have been much different for Clarke's side.
Stuart Armstrong looked to have skipped beyond Hungary's Willi Orban in the 80th minute, before the RB Leipzig defender grappled across the midfielder, with both tumbling inside the area.
Referee Facundo Tello waved away Scotland's appeals, and a subsequent check by VAR deemed the challenge not worthy of awarding a spot-kick.
“It was 100% a penalty," Clarke said. "Somebody, somewhere has to explain to me why that's not a penalty. It’s a one goal game, we get the penalty and it could have been a different night.
“I've got other words, but I'm not going to use them. I don't understand how VAR can look at that and say it's not a penalty.
“In a European competition, it may have been better to have a European referee but we had European VAR and maybe a referee didn't see the challenge clearly on the pitch, so what's the purpose of VAR if they are not going to come in on something like that. It was a penalty.”
Having qualified for successive European Championships, this was Scotland’s 12th major tournament group stage, and in 50% of those they have failed to win a single match – at the 1954, 1958, 1986, and 1998 World Cups and EURO 2020 and 2024.
“We gave everything, there’s nothing you can fault there. It was a very tough game against a good opponent," said Clarke. "A very close game that was always going to be decided by the first goal. You could tell that after half an hour.
“Unfortunately for us when we opened up towards the end of the game to try and chase the winner, that we felt we needed to get to the next stage, we got caught on the counter.”
Steve Clarke's side know a victory is a must to give them the best chance of qualifying for the knockout stages of a major international tournament for the first time in their history.
Scotland have won two of their last three meetings with Hungary (L1), with this their first encounter since a 1-0 away win in March 2018.
Following their 5-1 thrashing to hosts Germany in their opening game, an injury-hit Tartan Army got a point on the board against Switzerland to keep their hopes of qualification alive.
"We've obviously had a lot of injuries along the way - but us Scots are best at enduring adversity," said McGinn. "Hopefully we can prove a lot of people wrong.
"We have players who've been involved in high-pressure matches, but we're not feeling pressure, we feel anticipation about being that team who changes things for Scottish football.
"I don't think a lot of people across Europe thought we could do it, so we want to be the ones who do.
"We all know the magnitude of the occasion. We have the chance to write our name into the history books."
A win for Clarke's side would put them on four points from their three group games which in previous tournaments, has proved enough to qualify as one of the best-ranked third-placed sides.
Hungary arrived in Germany on the back of a 14-game unbeaten run, but are winless in their last eight Euros matches (D4 L4). However, the Scotland head coach is not underestimating his opponents despite their form at the tournament.
"Nothing except three points for us is what we're thinking," said Clarke. "We need to get three points to at least finish third in the group and we'll see where that takes us in the competition.
"Everybody knows how big a game it is. You can talk and talk and talk about it.
"We probably did a little bit too much with the first one, so we're trying to underplay this one, if you ever can with a game of this magnitude. But we're trying to make sure we're well prepared and ready to go."
The visitors started well and hit the goal frame through Ryan Christie but the Dutch took the lead five minutes from the break with a Tijjani Reijnders drive.
Scotland striker Lawrence Shankland hit the bar in the 62nd minute with only goalkeeper Mark Flekken to beat and they were made to pay 10 minutes later when Georginio Wijnaldum headed in a second.
Goals from substitutes Wout Weghorst and Donyell Malen in the 84th and 86th minutes then made it six games without a win for the Scots, with 18 goals conceded ahead of the friendly against Northern Ireland at Hampden Park on Tuesday night.
Scotland have not gone six matches without a win since a run from October 2007 to September 2008 and Clarke said: “We lost 4-0 which is painful.
“The players are suffering and I am suffering but there was lot of good stuff, we were very competitive with a good Dutch team for 70 minutes.
“It’s a lot of goals (18) and if you concede that amount of goals you are not going to win games.
“We spoke about it before so obviously we know we have to tighten up.
“The reaction to the second goal so probably something we need to think about, how we dig in and show we are hard to beat and if it finishes 2-0 it finishes 2-0.
“We have to be a bit more streetwise against the top teams and they are a top team.
“I didn’t say a lot after it, when emotions are as high as they are after a sore defeat it is better to go back to the hotel.
“I will sit with my staff, analyse the game and try to prepare something that we can show to the players tomorrow.
“No wins in six so we have to stop that on Tuesday night.
“But there is a lot to be positive about. People can look at the scoreline and go negative, that’s up to them.
“For 70 minutes… really competitive against a top side, we can take a lot from that. We have to analyse the last 20 minutes or so and look to do better.”
There had been a clamour for Shankland to start and despite his glaring miss, Clarke gave his backing to the Hearts captain.
He said: “He’s a striker, people forget strikers miss a lot as well as score a lot of goals, they gave to be in the right position and do the right thing.
“Lawrence will score goals in the future.
“I thought his all-round play was good, he didn’t let his side down.”