The former Dollar star was joined by Martina Navratilova for the challenge, which saw the pair attempt to collect water in the cup in order to gain access to the chest's key.
After leaving the camp, the couple strode through the forest where they were eventually greeted by a giant tea pot.
Upon closer inspection, they found a note which read: "I'm a little tea pot short and stout, I fire tea balls from my spout. When I hit a target, tea falls out, catch it all, then drain it out."
Tennis legend Martina immediately attached the strainer, cup and saucer to David's head and made him stand underneath a water container.
She then began loading the tea pot with tennis balls, which she had to fire at plates dangling from trees. When a target was hit, the container was tilted, covering David in water. The more water that got into the cup, the easier it would be for Martina to locate the key.
As the game got underway, David joked: "Is this how you won Wimbledon?"
Martin soon hit her stride, and replied: "Yes, this is how you win Wimbledon."
The pair eventually managed to get enough water into the cup to retrieve the key, and promptly returned to camp where they discovered they would need to answer 12 questions relating to their time in the jungle.
As well as answering a number of queries about past trials, the group - Marina, David, Joe Swash and George Takei - were also asked some more light-hearted ones, with Joe quick to remember that 'Pinky and Perky' was the nickname he gave Nicola's breasts.
Certain they had answered all 12 questions correctly and so were in for a treat, the group were devastated to learn they had actually got two wrong and so for the first time in the series had failed.
However, Joe's sorrow was short lived - he was delighted when it was revealed the group was to receive two inflatable donkey suits.
A less-excited David moaned: "We stood under 500 pails of water for you to wear that bloody suit."
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