Hillary Clinton has appeared in more than 30 primary debates during her two presidential campaigns, a deep history she can draw upon as she faces Donald Trump on Monday

WHITE PLAINS, N.Y. — Hillary Clinton has appeared in more than 30 primary debates during her two presidential campaigns, a deep history she can draw upon as she faces Donald Trump tonight.

Clinton has been through the debate gauntlet in two New York Senate campaigns as well as in presidential primary match-ups against then-Sen. Barack Obama in 2008, Vermont Sen. Bernie Sanders this year and other challengers.

Here’s a look at some key moments of Clinton’s past debates that could influence her performance against Trump:

BULLYING CAN BACKFIRE

Clinton’s first 2000 Senate debate with Republican rival Rick Lazio, then New York congressman, shows what could go wrong for Trump if he tries to bully her.

Lazio infamously walked over to Clinton’s podium during the debate, demanding she sign a pledge to forgo a form of donations known as soft money. “Sign it right now,” Lazio scolded Clinton, who gamely responded, “We’ll shake on this, Rick.” The move backfired with many female voters, who thought it was inappropriate.

HAVING IT BOTH WAYS

Clinton vacillated during an October 2007 debate in Philadelphia when she was asked if she supported her home state governor’s proposal to grant driver’s licenses to immigrants living in the country illegally.

Obama and John Edwards pounced, accusing her of trying to take multiple sides of the issue. “I can’t tell whether she was for it or against it,” Obama said. Her tortured response encouraged her opponents to accuse her of being disingenuous. Against Trump, it’s an example of how a defensive, legalistic response could hurt.

HUMOR HELPS

When Clinton was asked in 2008 by a New Hampshire moderator if she was likable enough, she responded with humor. “Well, that hurts my feelings,” she said as the audience roared. Obama responded, “You’re likable enough, Hillary.”

It came across as a putdown to many New Hampshire voters, who delivered Clinton a stunning victory. The exchange showed how Clinton’s humor could be an effective countermeasure to Trump.

WHEN THE GOING GETS TOUGH

Clinton and Obama engaged in one of their fiercest exchanges in January 2008, an episode that shows the risks of a drawn-out fight. Clinton refused to back down as tensions spilled out — a potential scenario against Trump.

Clinton and Obama battled over whether the Illinois senator had praised Republican ideals and former President Ronald Reagan. Obama said he was working in the streets while Clinton was “a corporate lawyer sitting on the board at Wal-Mart.” Clinton said she was fighting those GOP ideas while Obama was practicing law and representing real estate developer Tony Rezko “in his slum landlord business in inner-city Chicago.”

THE TAKEDOWN

One of Clinton’s strongest 2016 debate moments came before the New York primary, when she seized upon Sanders’ lengthy interview with the New York Daily News in which he struggled to explain how he would break up large Wall Street banks.

“Talk about judgment,” Clinton said in a stinging response, noting Sanders’ difficulty in explaining one of his “core issues.” It showed that if Clinton’s opponent reveals a weakness, she will take advantage of it.

THOSE EMAILS

In the first Democratic debate, Sanders declared that Americans were “sick and tired of hearing about your damn emails.” Clinton smiled broadly and laughed as the audience cheered. Sanders said voters cared more about economic issues, prompting Clinton to thank her opponent with a very public handshake.

Trump, who has repeatedly criticized Clinton’s use of a private email server, is unlikely to be as magnanimous.