Skip it.  Start reconciling as of 12/31/2013.  Enter the correct balance.  Clear everything except known outstanding.  For the difference, do a bank entry using the bank's GL account.

I have entered the correct "Statement Balance" as of 12/31/13. I have cleared everything using the "Quick Clearing". I have NOT yet touched the outstanding transactions.

1) When I look at the "Withdrawals Outstading", the amount it show is negative.

2) My "Book Balance" and "GL Balance" as of 12/31/13 do not match.

Please advise.

Do a bank entry using the bank's GL account to correct the book balance.

Well, I can't do a bank entry just yet since my out of balance is not zero.

Why is the Outstanding Withdrawals amount not zero when I have cleared them all in the Reconciliation Tab?

Yes, you _can_ do a bank entry, in fact, you _have_ to do a bank entry.  The reason it's not zero is you've never done a proper bank rec before.

The bank entry is done. Now my GL Balance match my Book Balance. Is it the next step to clear all transactions except outstanding and do a entry using a clearing account so I can bring my out of balance to zero?

Yes, except for the entry, you don't use a clearing account, you use the bank's GL account.

My out of balance is zero now after another bank entry. The statement and book balance are the same.

However, should I worry this balance is not matching my bank statement balance as of 12/31/13? If it doesn't matter, can I go ahead post the reconciliation and start 2014? Should I print any reports?

Perhaps some training is in order

If the 12/31/13 balance isn't the same, then do another bank entry until it is.

You can enter all transactions as "Bank entries" of the type withdrawal or deposit and use the gl account number of the bank itself so the GL effect is a wash. So, if there are some "transactions" that are uncleared as of the end of the year but part of the prior years GL Balance shee, you can enter them. The danger of not reconciling?

If you don't reconcile somewhere, there is a danger that transactions are posted to your company's bank account that are incorrect or fraudulent. Real Example. a client had a dishonest bookkeeper who was also the client's girlfriend. The bookkeeper was writing extra paychecks to herself and deleting them out of Quickbooks. She was also doing the "Bank Recs", but one day the client happened to open a bank statement and noticed. That said, he was unable to recover any of the money even though he was willing to prosecute.

Some clients don't use the Sage bank rec, instead preferring to reconcile to the balance sheet bank account balance. The problem with this is that the audit trail is more mysterious unless there are really good notes in the GL journal entries needed.  When possible, fix problems in the subledger in the subledger. But the point of making the GL balance tied to the bank rec balance plus deposits outstanding and minus withdrawals outstanding is to tie Sage 300 down to reality.