One of the most anticipated debates in modern American political history will get underway Monday night, when Democratic presidential nominee Hillary Clinton faces Republican rival Donald Trump on the same stage for the first time of their bitter and hard-fought contest for the White House.

Clinton is hoping to paint Trump as unfit for the presidency, while Trump is hoping to use his moment before the biggest audience he’s faced to date to assuage concerns about his temperament and knowledge of policy issues.

Analysts say a lot would be at stake for the two leaders as a single sentence or the slightest slip can do serious damage at this crucial time.

Trump – who nobody took seriously when he filed his nomination papers last year for the first time – has risen despite infighting to be the partys top candidate for the race to the White House but has faced flak for what many believe is a “hateful” rhetoric – against women, non- Americans, Muslims and so on.

Clinton, on the other hand, has been embroiled in questions about her family foundation and her use of a private email server while she was the secretary of state under incumbent President Barack Obama.

The controversies seem to have cost Clinton, who is eyeing to break the highest glass ceiling in the US and has constantly led in polls since this summer, the popularity as reflected in latest polls that have cut down her lead over Trump significantly.

The two candidates, who polls have also shown to be the least liked White House candidates in modern history, hope to use the debate to instil more confidence among voters.

The debate will also show if Clintons latest bout of illness, due to which she took a couple of days off from campaigning, has had any impact on the voters, even as Trump continued with campaigning till the last minute and had said he was “ready” for it.