Cayman national record holder Richard Collett ascends following a deep dive.

The first time Kurt Randolph dove below 80 meters on a single breath, the crushing pressure felt like an elephant standing on his chest.

Now, after back-to-back wins in the Deja Blue international free-diving competition, the Cayman Islands resident feels comfortable at depths most people consider impossible.

“The more you train, the more relaxed you feel under that pressure,” said Mr. Randolph after emerging from what for him was a relatively simple dip on the final day of competition.

Known as the “Ironman of free diving,” Deja Blue brings some of the world’s top free divers to Cayman every year. Because this competition involves six different disciplines, ranging from holding one’s breath in a pool to diving as deep as possible in the ocean, solid scores are required in every category to win.

“You don’t see the big numbers that you see in other competitions which focus more on depth,” said Mr. Randolph.

“Here, you have the pool too, so in the morning you are doing a depth dive and you have to be a bit conservative because then at night you have to take it into the pool and do laps. You have to strategize a lot more.”

Mr. Randolph, originally from the U.S., did not need to push his limits on the final day and was able to cruise through a 72-meter dive to record the victory.

“I did all my math last night, so I knew what I needed to do to get the win,” he said.

Other athletes did go for broke, however.

The rigorous safety procedures of tournament free diving make these competitions an attractive proposition for divers looking to push the boundaries in a safe environment.

Japanese free diver Tomoka Fukuda sat out the main competition to focus on inching toward her goal of hitting a world record 105-meter depth.

Earlier in the week, Ms. Fukuda became only the fifth female diver to hit the 100 meter mark. On Sunday, she fell just short of hitting 101 meters, blacking out at the surface after an otherwise successful dive.

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“I felt so good on the way down,” she said after the dive.

“But when I came up, actually I don’t remember anything, I blacked out at the surface.”

Surface blackout, caused by a lack of oxygen as the diver exhales after a long dive, is relatively common for free divers attempting to push the limits.

Divers are required to go through a surface protocol, demonstrating proper motor control, before a dive can be recorded as a success.

Ms. Fukuda said she was disappointed not to hit her target, but pleased with her progress on her first trip to the Cayman Islands, and determined to return and break the world record.

One diver who did hit her target was Shelby Eisenberg, who broke a U.S. national record by diving to 85 meters.

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She said the only way to operate at such depths is to take it second by second, kick by kick.

“Time does tend to go slowly down there,” she said, “but at the same time, it goes quicker than you think, because you are so active and so focussed on what you are doing.

“For me, after I get to the bottom, I have the ‘I got this’ feeling because you only have one way to go to finish the dive. You really have to stay focussed at that point because you are only halfway.”

The competition ran concurrently with the Cayman Open National Championships. Cayman’s Richard Collett was the winner of that competition, also placing third in Deja Blue, and breaking four national records in the process.

He said the highlight was hitting 63 meters and breaking the 200-feet barrier for the first time.

“It’s a rite of passage,” he said. “It is a milestone in your journey as a free diver. Everyone wants to hit the next marker.”