Hans Hateboer scored twice as Atalanta beat Valencia 4-1 Wednesday in the first leg of the Champions League's round of 16, putting the Italian team on the verge of a quarterfinal spot in its first season in the competition.

Roughly a third of the population of the small town of Bergamo was present at Milan’s San Siro stadium to see Hateboer, Josip Iličić and Remo Freuler score for Atalanta.

Substitute Denis Cheryshev scored a consolation goal for Valencia to give the Spanish team a glimmer of hope ahead of the second leg on March 10.

Leipzig, another team playing in the knockout stages for the first time, won 1-0 at Tottenham in Wednesday’s other Champions League match.

Atalanta qualified for Europe's top competition for the first time after a surprise third-place finish in Serie A last season. And it progressed to the knockout stages despite losing its first three matches in the competition.

It is playing its home matches at San Siro as its own stadium didn’t meet UEFA requirements. Bergamo has a population of approximately 122,000 and more than 40,000 had made the 60-kilometer journey.

Atalanta was forced into a late change as defender Berat Djimsiti picked up a knock during the warmup and had to be replaced in the starting lineup by Mattia Caldara.

The home side started brightly and Alejandro "Papu" Gomez sent a free kick narrowly over before Mario Pašalić forced a smart stop from Valencia goalkeeper Jaume Doménech.

Atalanta broke the deadlock in the 16th minute when Hateboer slid in at the back post to turn in Gomez's cross from the left.

Robin Gosens hit the side netting shortly afterward before Valencia got into the match and almost leveled on the half-hour mark following a quickly-taken free kick, but Ferrán Torres’ effort crashed off the right post.

Valencia went close again when Gonçalo Guedes’ cross-shot flew past Eliaquim Mangala sliding in at the far post.

But Atalanta doubled its lead three minutes from the break as Iličić held off two defenders before firing into the top left corner.

Atalanta dominated from the restart and Freuler extended his side’s lead in the 57th, curling a spectacular effort into the top right corner.

The noise in the stadium was ramped up even more five minutes later when Hateboer ran almost half the length of the pitch before shooting past Doménech.

Cheryshev replaced Guedes in the 64th and pulled one back for Valencia two minutes later, drilling a low shot into the bottom corner to give the Spanish side a glimmer of hope.

Leipzig beats Tottenham 1-0 in Champions League first leg

Timo Werner led Leipzig to its first Champions League knockout stage victory, netting a penalty to seal a 1-0 victory over Tottenham in the first leg of their round-of-16 meeting on Wednesday.

A clumsy tackle by Tottenham defender Ben Davies on Konrad Laimer led to the penalty that Werner converted in the 58th minute for his 26th goal of the season.

Such was the dominance of Leipzig — particularly in the first half in north London — that it was the German visitors that looked the more established Champions League side rather than last season's beaten finalists.

Tottenham's frustration was encapsulated by Dele Alli flinging his boot on the ground in annoyance while walking to the bench after being substituted.

Tottenham was already trailing at that point, and it took going behind to find the goal threat absent in the first half.

Giovani Lo Celso curled a free kick against the post and Lucas Moura headed wide on a night when Tottenham's shortage of attacking options was exposed.

With Harry Kane already sidelined, Son Heung-min joined the striker in the treatment room this week after surgery on an arm that could see the South Korean miss the rest of the season.

It is a season where Tottenham is struggling to qualify for the Champions League for a fifth successive season. Tottenham is a point behind fourth-place Chelsea in fifth in the Premier League, which would secure qualification if second-place Manchester City's European ban is upheld.

Leipzig is faring far better in Germany, sitting in second place in the Bundesliga.

Now the team is well-placed to make the Champions League quarterfinals in only its second season in the competition and a decade after playing in the fifth tier.

In Wednesday's other match, Atalanta routed Valencia 4-1 to close in on a spot in the quarterfinals in its first season in the competition.

The second leg is on March 10.