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Place the pineapple in the bowl of a food processor and pulse until pureed, stopping and scraping the sides of the bowl occasionally, 18 to 20 pulses. Pour into a Dutch oven.
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Place the winter melon in the food processor and pulse until very finely shredded, 20 to 22 pulses. Transfer to the Dutch oven.
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Cook the combined mixture over medium-high heat, stirring occasionally, until most of the liquid has evaporated and the winter melon begins turning translucent, about 20 minutes.
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Reduce the heat to medium, add the sugar, and cook until the mixture has thickened, about 8 minutes.
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Stir in the maltose syrup and cook, stirring constantly, until the mixture is very thick, sticky, and uniformly light amber in color, 10 to 12 minutes.
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Transfer mixture to a shallow bowl and refrigerate until cool. Divide into 1 Tsp each.