The Al Smith white-tie charity gala is traditionally a time when campaign hostilities are set aside as presidential candidates share a stage - often for the last time before election day. Not this year.
The Republican candidate drew boos and jeers from the well-heeled crowd as he took aim at Mrs Clinton, cutting close to the bone with a series of swipes referencing her emails scandal.
His Democratic rival wasn't to be outdone, however. She also elicited her fair share of awkward moments as she brought up sexual assault allegations surrounding Mr Trump and his alleged admiration for Russian president Vladimir Putin.
But it wasn't all mudslinging. Some of the biggest laughs of the night came when the candidates mocked some of their own campaign fails, including a speech made by Mr Trump's wife Melania, which was an almost word-for word-copy of an earlier speech delivered by Michelle Obama.
Here are some of the toughest put-downs of the night:
Donald Trump on Hillary Clinton
- "It's great to be here with a thousand wonderful people … or as Hillary calls it, her largest crowd of the season."
- "We have proven we can actually be civil to each other... Hillary accidentally bumped into me and she very civilly said 'pardon me'. And I very politely replied, 'Let me talk to you about that after I get into office.' Just kidding, just kidding."
- "Last night I called Hillary a nasty woman. But this stuff is all relative. After listening to Hillary rattle on and on and on. I don't think so badly of Rosie O'Donnell anymore. In fact I'm actually starting to like Rosie a lot."
- "I'd like to address an important religious matter, the issue of going to confession. Or as Hillary calls it, the 4th July weekend with FBI director Comey."
- "Hillary believes that it's vital to deceive the people by having one public policy and a totally different policy in private," he said to growing jeers. "Here she is tonight, in public, pretending not to hate Catholics."
Candidates shake hands at the end of the charity dinner | Photo: PA Images
Hillary Clinton on Donald Trump
- "Donald, after listening to your speech, I will also enjoy listening to Mike Pence deny that you ever gave it."
- "People look at the Statue of Liberty and they see ... a beacon of hope for people around the world. Donald looks at the Statue of Liberty and sees a four. Maybe a five if she loses the torch and tablet and changes her hair."
- "You notice there is no teleprompter here tonight which is probably smart, because maybe you saw Donald dismantle his prompter the other day. And I get that, they are hard to keep up with, and it's probably even harder when you're translating from the original Russian."
- "Donald really is as healthy as a horse, you know, the one Vladimir Putin rides around on."
- "I have great respect for people like Kellyanne Conway. She is working day and night for Donald and because she is a contractor he is probably not going to even pay her."
- "Donald, if at any time you don't like what I'm saying, feel free to stand up and shout wrong while I'm talking. Come to think of it, it's amazing I'm up here after Donald. I didn't think he'd be ok with a peaceful transition of power."
- "Donald has no policies, I keep hearing that. I'd actually like to defend him on this. Donald has issues. Serious issues. Really, really serious issues."
Candidates take aim at themselves
Hillary Clinton: "This is such a great event, that I took a break from my vigorous nap schedule."
Donald Trump: "I have to say the media this year is more biased than ever before. You want the proof? Michelle Obama gives a speech and everyone loves it, it's fantastic, they think she is absolutely great. My wife Melania gives the exact same speech, and people get on her case. And I don't get it, I don't know why."