Ok, I said I was going to do it and so I did. I went and downloaded the newest version of iTunes and upgraded my Winamp also to the newest version and put the programs head to head.

***Please note this isn't just me out to prove that one program is better than the other! I am simply out to compare the two and determine which of the two is the better programs ***

Download:
Winamp by far. The file for winamp is just over 6mb's while the file for iTunes was almost 30mb's.
+1 Winamp

Installion:
Winamp wins heres. The configuration options and overall time is better than iTunes which wants to install Quicktime and doesn't offer and configuration options that aren't very useful.
+1 Winamp

First Run:
For users that just want the music to play and don't care how it is done, iTunes is for you. But if you are picky about how files are organized and where they reside, I would choose Winamp. When you first load iTunes, it will scan your pc for audio and video files and then start to convert audio files it doesn't like. This is very annoying, because not only does it convert the songs, it creates a new folder in your my music and puts the new copies of the songs there, effectively creating two files for each song. Winamp on the first run allows you to choose where to scan for audio and doesn't need any converting.
+1 Winamp

Plug-ins:
This is a big selling point for me. When you have a program that is meant to be dynmatic enought to play media files, you need to have plug-ins. But plugins for iTunes are far and few between. For example I looked for a iTunes plugin to play the file type WV, but I couldn't find one. After a short search one was found for winamp.
+1 Winamp

Layout:
At first glance iTunes is the better layout, but if you take 5 minutes to go about and play with winamp you will find that it is the better layout. Now before you disagree with me, try it. I only use the librry screen on Winamp which offers everything iTunes does, but in a cleaner and easier to follow manner.
+1 Winamp

Radio:
This one is tough to give the nod to, so I am going to call it a draw. While iTunes has the radio channels built into the program, it doesn't have near as many as winamp where you just go to there site to browse through the list. But if you find a channel you like in iTunes you can't bookmark it for easy nav next time, where as in Winamp you can so you can skip the site and just go your bookmarks.
N/A

Podcast/ShoutWire:
Podcast wins. Though shoutwire is older (from my understanding) it has nothing on podcasting. With pod casts you can get video while with shoutcast I have only seen audio and text. Plus most of the shoutwires are older and the community seems to be dieing. Shoutcast is only really useful if you are actually looking for it. You don't have a centralized directory like the podcasts.
+1 iTunes

Streaming:
I have no clue how to stream in iTunes. Its simple enough to listen to a stream. You just get the URL or addy and plug it in. For Winamp playing a stream is just a easy, just plug in the URL you want to tune into. But to stream in winamp, you will need a plugin call Shoutcast. I've only done a little shoutcasting myself last year so I dunno how much it changed but was simple enough. You run it and your play now list could be streamed to those that were listening. So on the basis I dunno know to do it in iTunes I will give neither the nod.
N/A

Skins:
This also doesn't really mattter to me, but I will review it just for those that care. iTunes has a fair number of skins, but overall they suck. Unlike winamp, all the iTune skins do is change the colors, whereas with Winamp the skins can change the total look and real of the program. And has a huge skinning community.
+1 Winamp

System Resources:
This was a hands down win for Winamp. My test was for both to play a internet daio station.

Winamp (total) : 15 000K of sys mem
iTunes (total) : 49 000K of sys mem
+1 Winamp

Video:
I don't know why, but when I had iTunes scan my media library it didn't pick up several of my videos. May just be a glich or something but I thought I would note it. These are basically the same but again winamp takes the lead but only very slighty here. For iTunes when you play a video it opens a seperate window using Quicktime but file info (such as time and postion) are on the iTunes screen. Also just a plus to winamp is that you can use the file browser to find a file instead of just the library.
+1 Winamp

HotKeys:
Both programs have then, but Winamp allows to you customize and add new hotkeys for every function in the program while with iTunes you can only use the premade ones.
+1 Winamp

Sharing:
iTunes won this one hands down with being able to share your whole library or just playlists across a network. (*This in my opinion is the only reason it is so popular amoung university students*) Where with winamp, it isn't even possible without a plugin. There is a plugin for it, but I haven't had a chance to test it. But with the plugin it, the developer plans it make it so that you can download songs from those you connect to. So if this actually happens Winamp to get this point but for now it will belongs to iTunes
+1 iTunes

Playlists:
There is no difference between these two. I don't really see how you can this screw up so neither get anything for this
N/A

Closing Notes:
As I finally finish playing with these programs, I would like to voice a few qualms. With Winamp, while in the library there is no track info. And in iTunes, the overall simplicity is annoying. Many features and options have been axed it seems making it difficult for those that like to customize.

In the end both are good programs, and if you have an iPod you will want iTunes since you need it to connect to your iPod (I think... I don't own one) but if you don't own an Ipod, I would give the final nod to Winamp

Winamp = 9/14
iTunes = 2/14
N/A = 3/14

Final Verdict:
iTunes = Uninstalled