Need to replace pdf file on existing website. Please help!

Our intern left this summer and we're clueless about Dreamweaver. We have a Spry Menu with a link to a pdf file of our employment application. Our application has been revised, and we need to replace it on the website.
From what we have gathered, Spry Menu Widget is no longer available to download and we are unable to change the link to a new file via the widget because intern took his laptop with the widget installed.
So to make do, I have downloaded the files from the website to my Local folder, deleted the old employment application pdf file and have replaced it with the new application with the exact same file name as the old one.
My question is.... If I highlight the new application in our local folder and click upload, should this make the link in the menu bar go to the new application?
Thanks for you help in advance!

Ok, sure. So we needed to replace a pdf file that was linked from our spry menu bar. We didn't have the widget and didn't think we could download it, so we went to the folder on the bottom right hand side of the screen and opened the remote folder. We then highlighted all of those files except for the / file at the very top. We then clicked the down arrow to copy those files into our local folder. Once they were downloaded, we went into the local folder and found the file we needed to switch out. We then deleted that file, named our new file the exact same file name, and clicked and dragged it from our computer onto the same folder that contained the file we deleted. We then highlighted that file, right clicked and chose "PUT", as Jon had instructed us to do above. It uploaded the file. When it was finished, we checked our website and got an error because the pages wouldn't load. However, a few minutes later we tried again and everything worked perfectly. The new pdf file had replaced the old one and still linked properly from the menu bar.

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