Will a tiger and monkey match ever work?

Yes. Just be willing to have healthy boundaries and compromises and honor each other’s intelligence and should go smoothly. Communication and being able to relate to each other is what makes a “relationship”.

Better stay off monkeys if you are looking for something long term. They are highly narcissistic by nature while we tigers are most on the empathic side (recipe for a toxic relationship) - I had several experiences with monkey girls - all with bad endings. Better don't waste your time and energy there. Our best matches as tigers are horses, pigs and dragons/dogs.