It depends,  Massachusetts purposes, losses up to winnings are not deductible even if they may be claimed as an itemized deduction on U.S. Form 1040, Schedule A. It does not follow Federal rules.

Massachusetts does allow the cost of any winning ticket or chance to be deducted from the winnings received from such ticket or chance.

Please see this Massachusetts link, please look at Example #1 to Illustrate Mass vs. Federal Reporting of Gambling Winnings and Deductions for more information: http://www.mass.gov/dor/individuals/filing-and-payment-information/guide-to-personal-income-tax/mass...