Wood that is used in outdoor applications is frequently exposed to weathering and is thus prone to fungal degradation. Ways to prevent fungal degradation include keeping the wood dry. The majority of hydrophobic and wood modification systems have been tested only on freshly treated wood. Little information is available on how various wood-based materials perform after a certain period of weathering. To elucidate this question, 17 wood samples were tested from the following species: oak (Quercus), sweet chestnut (Castanea sativa), European larch (Larix decidua), Scots pine heartwood and sapwood (Pinus sylvestris), Norway spruce (Picea abies), and beech (Fagus sylvatica). Moisture performance of the wood samples was improved with thermal modification, wax, oil, and biocide treatment. Specimens were exposed to various degradation-aging factors (blue stain fungi, decay fungi, artificial weathering, and natural weathering). Various moisture performance tests were applied before and after aging: short-term water uptake (tensiometer), long-term water uptake, water vapor tests, drying tests, etc. The water exclusion efficacy of wood was decreased after aging. Aging factors were found to act synergistically and to have a more prominent influence on less durable wood compared to durable or preservative-treated wood. Wax-treated wood performed best, regardless of which moisture performance test was applied.