Unfortunately you cannot use your map data for OpenStreetMap. Why? Because of the following:

OpenStreetMap is about free maps based on the effort of volunteers to do the mapping by going down the streets themselves. Uploading derived work from copyrighted maps (such as the military maps) is forbidden. Doing so will eventually cause OpenStreetMap to become subject to law suits from copyright holders. This would probably mean the end of the project.

So to put it simple: do not upload material that is scanned, drawn over or otherwise copied from copyrighted maps or other sources that do not comply to the OpenStreetMap licence CC-BY-SA.

More info is in the legal FAQ.

If you have maps or tracklogs that are completely based on data that you gathered yourself then it is no problem to contribute that to OpenStreetMap ofcourse. You’ll need to convert the data to a dataformat that OSM can understand. Then you can bulk-import it to the server. The JOSM data format is very similar to the OSM XML-schema.