Input/Output Hidden Markov Models (IOHMMs) are conditional hidden Markov models in which the emission (and possibly the transition) probabilities can be conditioned on an input sequence. For example, these conditional distributions can be linear, logistic, or non-linear (using for example multi-layer neural networks). We compare the generalization performance of several models which are special cases of Input/Output Hidden Markov Models on financial time-series prediction tasks: an unconditional Gaussian, a conditional linear Gaussian, a mixture of Gaussians, a mixture of conditional linear Gaussians, a hidden Markov model, and various IOHMMs. The experiments compare these models on predicting the conditional density of returns of market and sector indices. Note that the unconditional Gaussian estimates the first moment with the historical average. The results show that, although for the first moment the historical average gives the best results, for the higher moments, the IOHMMs yielded significantly better performance, as estimated by the out-of-sample likelihood.