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<<So does this mean that if I open a Roth IRA on 1/5/99 that I can contribute $4000 and say it's for
1998/99?>>

Yes, but to eliminate any confusion I'd give your custodian 2 checks with 'Tax Year 1998 Contribution' written on one & 'Tax Year 1999 Contribution' written on the other. IMO, if you have the money now, go ahead & open the account & put your $2K ASAP. That way your money gets tax sheltered 4 months earlier.

<<Does this also mean that I can continue to contribute $2000 on 1/5 each and every year after that?>>

You can contribute on 1 January of a particular year (or anytime up until 15 April of the following year), the fact that you opened the account on 5 January is meaningless. Also remember that your contributions to all your IRAs (Roth & Traditional) cannot exceed $2K total for a given tax year.

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