Calculate balance for every row by sequentially subtracting each row's amount from an initial sum
This is a "running total" type of problem: each row's total is calculated based on that row's value added to, or subtracted from, the previous row's total.

Since you are using SQL Server 2014, Transact-SQL has built-in syntax available to you to help you with getting the results.

Using the simplified model of "One deposit per month, many withdrawals per month", the SQL statement could go like this:

SELECT
  d.TotalAmount,
  w.WithdrawAmount,
  Balance = d.TotalAmount - SUM(w.WithdrawAmount) OVER (ORDER BY w.WithdrawDate ASC)
FROM
  dbo.Deposit AS d,
  dbo.Withdrawal AS w
WHERE
  d.DepositDate  >= start_of_this_month AND d.DepositDate  &lt; start_of_next_month
  AND
  w.WithdrawDate >= start_of_this_month AND w.WithdrawDate &lt; start_of_next_month
;

The WHERE clause is supposed to filter the tables down to one deposit row from Deposit and the however many corresponding withdrawals from Withdrawal. If the tables support multiple accounts and the amounts need to be further related by account, you may want to replace the FROM clause with something like this:

FROM
  dbo.Deposit AS d
  INNER JOIN dbo.Withdrawal AS w ON d.AccountNumber = w.AccountNumber


The SUM(w.WithdrawAmount) OVER (ORDER BY w.WithdrawDate ASC) expression calculates a running WithdrawAmount total for each row. So, the total increases with each row (sorted in the ascending order of WithdrawDate) – thus with each row an ever increasing amount is subtracted from TotalAmount, drawing Balance nearer to 0.

The above query will give you each row's balance but not the status. To get the status, you will need to reference the Balance value to compare it 0 and select a corresponding status string to return. Balance is a calculated column and in order to be able to reference it you need to nest the above query and reference Balance at the outer level. Nesting could be done with either a derived table or a common table expression (CTE). This query uses a CTE:

WITH balances AS
  (
    SELECT
      d.TotalAmount,
      w.WithdrawAmount,
      Balance = d.TotalAmount - SUM(w.WithdrawAmount) OVER (ORDER BY w.WithdrawDate ASC)
    FROM
      dbo.Deposit    AS d,
      dbo.Withdrawal AS w
    WHERE
      d.DepositDate  >= start_of_this_month AND d.DepositDate  &lt; start_of_next_month
      AND
      w.WithdrawDate >= start_of_this_month AND w.WithdrawDate &lt; start_of_next_month
  )
SELECT
  TotalAmount,
  WithdrawAmount,
  Balance,
  Status = CASE WHEN Balance > 0 THEN 'StillAvailableYAY' ELSE 'ZeroBalanceOops' END
FROM
  balances
;

Of course, if you do not really need to return the balance – only to compare it to 0, then nesting is not needed and you can put the d.TotalAmount - SUM(w.WithdrawAmount) OVER (ORDER BY w.WithdrawDate ASC) expression directly into the CASE, replacing Balance.