Thank you DarthKenobi for accepting this debate, let’s get started.
I will make my appeal that Sola Scriptura is a self-defeating doctrine with 3 main arguments.
1. Not a biblical doctrine
2. The Bible is not "self-authenticating"
3. The Disaster of sola scriptura
Not a biblical doctrine
It would seem that for a doctrine with the title Sola Scriptura (the Bible alone) there should be sufficient biblical evidence that the bible commands such a practice. Some point to Mark 7:7-8 as a declaration that Jesus condemns all traditions not found in the scriptures. The historical understanding of this text is not a condemnation of all traditions but rather of ones made by men for their own purpose. In fact we see in the writings of St. Paul a command to the churches to hold to traditions taught by the Apostles.
"Now I praise you because you remember me in everything and hold firmly to the traditions, just as I delivered them to you." (1 Corinthians 11:2)
"So then, brethren, stand firm and hold to the traditions which you were taught, whether by word of mouth or by letter from us." (2 Thessalonians 2:15)
"Now we command you, brethren, in the name of our Lord Jesus Christ, that you keep away from every brother who leads an unruly life and not according to the tradition which you received from us." (2 Thessalonians 3:6)
These passages are very difficult to reconcile with Sola Scriptura. Why would the inspired authors command his readers to "hold to the traditions which you were taught, whether by word of mouth or b letter from us" if the bible alone would suffice? Surely there must be some explicit demand in the bible to take only what is found in scripture and not a word else. No such command is found in scripture. It must be remembered that I am not saying the bible isn't the inspired "God-breathed" Word of God. I am stating the bible never teaches that the bible alone is enough and in fact it teaches the opposite.
The Bible is not "Self-Authenticating
This may be the most troublesome aspect of the Sola Scriptura doctrine, the bible doesn't self-authenticate. What do I mean by this? I mean that the bible doesn't explicitly say which books are inspired; in effect the table of contents didn't fall from heaven. It is a matter of historical fact that before that the Synod of Rome (382 A.D) there was no official canon of the Bible . So any appeal to the scripture as the sole authority is actually appealing to the authority of the Church to decide on the scripture. This is an unavoidable problem that those who promote Sola Scriptura face.
"The only authority which non-Catholics have for the inspiration of the Scriptures is the authority of the Catholic Church." (The Faith of Millions, p. 145) 
For instance because the bible has no inspired "table of contents" the protestant revolted Martin Luther wished to take out books from the new testament that he didn't like. Had Luther had his way Hebrews, James, Jude, and Revelation would all be excluded from the bible . Since the bible is not self-authenticating there is no biblical reason to stop him.
The Disaster of Sola Scriptura
According to the most conservative estimate available there are currently 8,196 protestant denominations in the world today . All of these denominations have the same bible. All of these denominations claim to be led by the Holy Spirit, so why all the confusion? Well if Pastor John interprets one passage one way, and Deacon Jim doesn't like it, then who’s right? In Sola Scriptura there is not authority to INTERPRATE the word of God. No pastor has any more authority than another pastor to declare the meaning of difficult phrases in the bible.
We must also remember that these differences are not all minor but many are in the order of salvation. Is baptism a sign or does it confer regeneration to the soul? Is the saving work of Jesus for everyone or only for a select few? Are speaking in tongues a valid gift? These and countless other disputes cannot be solved by the bible alone because no one can say "Thus says God".
Even Martin Luther saw the ramifications of Sola Scriptura at the end of his life when he famously said "there are now as many doctrines as there are heads” 
In conclusion the doctrine of sola Scriptura is neither biblically sound, nor logically possible (given no self-authentication). And lastly it is the cause of so much confusion among Christians.