"Shark Tank" star Robert Herjavec stunned viewers in May by making a handshake deal to invest $5 million in Zero Pollution Motors, maker of a $10,000 plastic mini car that runs on compressed air. The deal would have doubled the previous record for the largest "Shark Tank" investment ever, but it ultimately fell apart during the due diligence process. Still, a handful of entrepreneurs have successfully attracted million-dollar investments from the sharks.

Here are the five largest deals made on "Shark Tank" where money actually wound up exchanging hands.

—By Graham Winfrey, special to CNBC.com
Posted 22 June 2015

Entrepreneur Charles Michael Yim made history in more ways than one during Season 5 of "Shark Tank." On top of landing the show's largest deal at the time—$1 million for his smartphone breathalyzer company Breathometer—Lim was the first to partner with all five sharks.

Mark Cuban paid $500,000 for 15 percent of the company, while Lori Greiner, Robert Herjavec, Daymond John and Kevin O'Leary split the remaining $500,000 investment. The 30 percent equity stake Lim gave up seems to have been worth it: A year after the segment aired on the show, Breathometer's sales hit nearly $10 million, up from $1 million just a few months earlier.

Austin, Texas-based BeatBox Beverages didn't reinvent the wheel with its product: wine in a neon-colored package designed to look like a boom box. But Justin Fenchel and his co-founders did walk out of the tank during Season 6 with a huge check from Mark Cuban.

They initially asked for $250,000 for 10 percent equity, but ended up with a much sweeter deal: $1 million for a third of the company. Sales reportedly have surged following the business's appearance on the show last October.

The founders of Rugged Events, which hosts of a 5-km race through a muddy course called the Rugged Maniac Obstacle Race, entered the tank during Season 5, seeking $1 million for 10 percent equity.

After fielding multiple offers for a piece of the company, which had $4.2 million in annual sales at the time, co-founders Rob Dickens and Brad Scudder accepted $1.75 million for 25 percent from Mark Cuban. Since then, revenue reportedly has grown by $1 million.

In Season 5, entrepreneur Melissa Carbone struck a $2 million deal with Mark Cuban for 20 percent of her horror entertainment company, TenThirtyOne Productions, claiming what was then the largest deal ever on "Shark Tank."

With Cuban's help, Carbone's business, which creates and produces live Halloween-themed attractions, inked a partnership with Ticketmaster and received a separate investment from Live Nation, the largest concert company in the country.

Kevin O'Leary, aka "Mr. Wonderful," struck the largest deal in "Shark Tank" history during Season 6 by loaning the single-serve wine company Zipz $2.5 million in exchange for 10 percent equity. O'Leary even negotiated the right to buy another $2.5 million worth of equity from Zipz founder Andrew McMurray at the same valuation in the event of an exit.

The deal went through, and O'Leary said he expects the company to have a game-changing impact on the U.S. beverage market, though it likely will take multiple years.