Drain the cherries and then puree them in a blender or food processor.
In a medium size pot, bring pureed cherries, balsamic vinegar, garlic, and sugar to a boil. Reduce heat and allow mixture to simmer uncovered for 10 minutes.
Pour the cooked mixture in a standing mixer or blender. Mix in red wine vinegar, salt, and pepper. While mixing, slowly pour in the oil and beat for 2 more minutes.
Store in jars in the refrigerator for up to two weeks.