Morocco edged past Canada to top Group F and reach the World Cup knockout stage for the first time in 36 years while Belgium have been bokted out of the competition after playing a goalless draw against Croatia.
The Atlas Lions, whose previous trip to the last 16 came in 1986, finished above 2018 finalists Croatia, while Belgium - ranked second in the world - are out after finishing third in the group.
A tough test awaits in the next round against the team that finishes second in Group E, which could potentially be Spain or Germany.
Morocco went ahead after just four minutes courtesy of a goalkeeping howler from Milan Borjan.
The Canada keeper sprinted out of his goal but passed the ball straight to Hakim Ziyech, who lofted a cool finish into an open net from 30 yards.
The north African side doubled their advantage through Youssef En-Nesyri's well-taken goal as he controlled Achraf Hakimi's superb pass before firing in.
But sloppy defending gave Canada a route back into the game when West Ham's Nayef Aguerd stuck a boot out to divert the ball into his own net - the 100th goal scored at this World Cup.
Knowing if they avoided defeat they would go through, Morocco were happy to sit back and soak up pressure in the second period.
But Atiba Hutchinson came close with a header that rattled the crossbar and dropped down onto the line as Canada's campaign ended without a point.
Morocco march on
Morocco didn't win a game at the last World Cup in Russia but have turned on the style this time, becoming the second African team after Senegal to make it through.
Cameroon play Brazil (19:00 GMT) and Ghana face a grudge match against Uruguay in the final round of group fixtures on Friday to determine whether they can make it a total of four from the continent.
Morocco manager Walid Regragui has a team which is full of players with big game experience.
Chelsea's Ziyech, who has been off the boil for his club, has found form for his country and grabbed the opener, which was gifted to him by Borjan.
Hakimi and En-Nesyri, a regular scorer in the Champions League, combined for the second as the Sevilla player latched on to the Paris St-Germain full-back's pin-point pass before smashing in.
He could have had a second but a stunning volley was ruled out for offside.
Before the game, Morocco had kept a clean sheet in all six matches under Regragui but that record went when Aguerd poked into his own net before the break.
Canada probed for a way back in the second half and although Hutchinson came close with a header which hit the woodwork, they failed to produce a shot on target in the match.
Star man Alphonso Davies stabbed a chance wide, meaning his side have now lost all six of their World Cup games, a feat only achieved previously El Salvador.
They produced another lacklustre display against Croatia despite knowing victory was necessary to progress to the last 16.
Substitute Romelu Lukaku had numerous chances in the second half but his failure to convert any sealed his country's fate.
Lukaku, searching for sharpness following injury, hit the post from in front of goal, poked an effort wide when well-placed and reacted too slowly when the ball hit him in the six-yard box in stoppage time.
Croatia, finalists in 2018, got the point they needed to progress from Group F as runners-up, with Morocco taking top spot thanks to a 2-1 win against Canada.
Zlatko Dalic's side will face the winners of Group E - which is currently Spain - in the last 16.
Elsewhere, Belgium have been knocked out of the World Cup at the group stage as Croatia progressed at their expense with a goalless draw in Qatar.
Roberto Martinez's side, who finished third in Russia four years ago and are ranked second in the world, have had a disappointing tournament with just one win and one goal in their three matches.
They produced another lacklustre display against Croatia despite knowing victory was necessary to progress to the last 16.
Substitute Romelu Lukaku had numerous chances in the second half but his failure to convert any sealed his country's fate.
Lukaku, searching for sharpness following injury, hit the post from in front of goal, poked an effort wide when well-placed and reacted too slowly when the ball hit him in the six-yard box in stoppage time.
Croatia, finalists in 2018, got the point they needed to progress from Group F as runners-up, with Morocco taking top spot thanks to a 2-1 win against Canada.
Zlatko Dalic's side will face the winners of Group E - which is currently Spain - in the last 16.
Belgium players fell to the turf at full-time as their supporters behind the goal politely applauded them off the pitch.
Lukaku, who replaced Dries Mertens at half-time, came into the game with intent and immediately brought energy and purpose to his side.
But his missed opportunities in the second half proved costly, with each one bringing an audible collective groan from the stands and the on-loan Inter Milan striker the punched the dugout in frustration after the final whistle.
Croatia were unconvincing - they had a penalty ruled out by VAR due to an offside in the build-up in the first half - but did enough to secure progression.
However they looked a level below what they showed to reach the final in Russia four years ago and their celebrations were fairly subdued after scraping through.
'Golden generation' fall at first hurdle
This Belgium side were ranked number one in the world in February and their collection of star names have been fancied to do well in recent tournaments - but their supporters are used to disappointment.
On the biggest stages, their 'golden generation' has not lived up to expectations, failing to reach a major final despite their array of talented players.
The team, whose key players are approaching the latter stages of their careers, probed for the breakthrough at the Ahmad Bin Ali Stadium but superstars Kevin de Bruyne and Eden Hazard could do little to change the result.
Croatia had the best chances in a poor first half as Ivan Perisic struck wide while Andrej Kramaric thought he had won a penalty following a foul by Yannick Carrasco, but it was later ruled out by VAR.
Lukaku's introduction had an immediate impact after the break when he pounced on a rebound from Carrasco's shot but struck it against the inside of the post.
Real Madrid midfielder Luka Modric went close when his poked effort was held by club team-mate Thibaut Courtois in a rare Croatia second-half attack.
But the biggest chances fell Lukaku's way, not least in the closing minutes when he deflected a cross wide then was slow to react and allowed the ball to hit his body and fall into the goalkeeper's arms from about two yards out.
A draw was probably a fair result and Belgium cannot have too many complaints at their failure to progress after a disappointing group stage.
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