﻿<?xml version="1.0" encoding="utf-8"?>
<Return xmlns="http://www.irs.gov/efile" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" returnVersion="2018v3.1">
  <ReturnHeader binaryAttachmentCnt="0">
    <ReturnTs>2019-12-13T15:20:19-06:00</ReturnTs>
    <TaxPeriodEndDt>2019-01-31</TaxPeriodEndDt>
    <PreparerFirmGrp>
      <PreparerFirmEIN>411414667</PreparerFirmEIN>
      <PreparerFirmName>
        <BusinessNameLine1Txt>ESTERBROOKS SCOTT SIGNORELLI ETAL LTD</BusinessNameLine1Txt>
      </PreparerFirmName>
      <PreparerUSAddress>
        <AddressLine1Txt>302 W SUPERIOR ST STE200</AddressLine1Txt>
        <CityNm>DULUTH</CityNm>
        <StateAbbreviationCd>MN</StateAbbreviationCd>
        <ZIPCd>55802</ZIPCd>
      </PreparerUSAddress>
    </PreparerFirmGrp>
    <ReturnTypeCd>990EZ</ReturnTypeCd>
    <TaxPeriodBeginDt>2018-02-01</TaxPeriodBeginDt>
    <Filer>
      <EIN>416038563</EIN>
      <BusinessName>
        <BusinessNameLine1Txt>DULUTH SAIL AND POWER SQUADRON</BusinessNameLine1Txt>
      </BusinessName>
      <BusinessNameControlTxt>DULU</BusinessNameControlTxt>
      <PhoneNum>2183106231</PhoneNum>
      <USAddress>
        <AddressLine1Txt>PO BOX 161074</AddressLine1Txt>
        <CityNm>DULUTH</CityNm>
        <StateAbbreviationCd>MN</StateAbbreviationCd>
        <ZIPCd>55806</ZIPCd>
      </USAddress>
    </Filer>
    <BusinessOfficerGrp>
      <PersonNm>LORI YECOSHENKO</PersonNm>
      <PersonTitleTxt>TREASURER</PersonTitleTxt>
      <PhoneNum>2183106231</PhoneNum>
      <SignatureDt>2019-12-11</SignatureDt>
      <DiscussWithPaidPreparerInd>true</DiscussWithPaidPreparerInd>
    </BusinessOfficerGrp>
    <PreparerPersonGrp>
      <PreparerPersonNm>MICHAEL A PEDERSON</PreparerPersonNm>
      <PTIN>P00454472</PTIN>
      <PhoneNum>2187276846</PhoneNum>
      <PreparationDt>2019-12-10</PreparationDt>
    </PreparerPersonGrp>
    <FilingSecurityInformation>
      <IPAddress>
        <IPv4AddressTxt>96.33.224.34</IPv4AddressTxt>
      </IPAddress>
      <IPDt>2019-12-13</IPDt>
      <IPTm>15:20:19</IPTm>
      <IPTimezoneCd>CS</IPTimezoneCd>
      <FilingLicenseTypeCd>P</FilingLicenseTypeCd>
      <AtSubmissionCreationDeviceId>E5FF54BAFE4714031E88029BA2A9C647CD32493C</AtSubmissionCreationDeviceId>
      <AtSubmissionFilingDeviceId>E5FF54BAFE4714031E88029BA2A9C647CD32493C</AtSubmissionFilingDeviceId>
    </FilingSecurityInformation>
    <TaxYr>2018</TaxYr>
    <BuildTS>2020-04-17 16:48:07Z</BuildTS>
  </ReturnHeader>
  <ReturnData documentCnt="4">
    <IRS990EZ documentId="RetDoc1" referenceDocumentId="RetDoc3">
      <GroupExemptionNum>1041</GroupExemptionNum>
      <MethodOfAccountingCashInd>X</MethodOfAccountingCashInd>
      <ScheduleBNotRequiredInd>X</ScheduleBNotRequiredInd>
      <WebsiteAddressTxt>DULUTHPOWERSQUADRON.COM</WebsiteAddressTxt>
      <Organization501c3Ind referenceDocumentId="RetDoc4">X</Organization501c3Ind>
      <TypeOfOrganizationCorpInd>X</TypeOfOrganizationCorpInd>
      <GrossReceiptsAmt>33917</GrossReceiptsAmt>
      <InfoInScheduleOPartIInd>X</InfoInScheduleOPartIInd>
      <ContributionsGiftsGrantsEtcAmt>3651</ContributionsGiftsGrantsEtcAmt>
      <MembershipDuesAmt>7464</MembershipDuesAmt>
      <InvestmentIncomeAmt>3</InvestmentIncomeAmt>
      <FundraisingGrossIncomeAmt referenceDocumentId="RetDoc2">21735</FundraisingGrossIncomeAmt>
      <SpecialEventsDirectExpensesAmt>13100</SpecialEventsDirectExpensesAmt>
      <SpecialEventsNetIncomeLossAmt>8635</SpecialEventsNetIncomeLossAmt>
      <GrossSalesOfInventoryAmt>586</GrossSalesOfInventoryAmt>
      <CostOfGoodsSoldAmt>483</CostOfGoodsSoldAmt>
      <GrossProfitLossSlsOfInvntryAmt>103</GrossProfitLossSlsOfInvntryAmt>
      <OtherRevenueTotalAmt>478</OtherRevenueTotalAmt>
      <TotalRevenueAmt>20334</TotalRevenueAmt>
      <FeesAndOtherPymtToIndCntrctAmt>395</FeesAndOtherPymtToIndCntrctAmt>
      <OccupancyRentUtltsAndMaintAmt>9308</OccupancyRentUtltsAndMaintAmt>
      <PrintingPublicationsPostageAmt>2327</PrintingPublicationsPostageAmt>
      <OtherExpensesTotalAmt>10902</OtherExpensesTotalAmt>
      <TotalExpensesAmt>22932</TotalExpensesAmt>
      <ExcessOrDeficitForYearAmt>-2598</ExcessOrDeficitForYearAmt>
      <NetAssetsOrFundBalancesBOYAmt>18887</NetAssetsOrFundBalancesBOYAmt>
      <NetAssetsOrFundBalancesEOYAmt>16289</NetAssetsOrFundBalancesEOYAmt>
      <InfoInScheduleOPartIIInd>X</InfoInScheduleOPartIIInd>
      <CashSavingsAndInvestmentsGrp>
        <BOYAmt>16532</BOYAmt>
        <EOYAmt>14454</EOYAmt>
      </CashSavingsAndInvestmentsGrp>
      <OtherAssetsTotalDetail>
        <BOYAmt>2355</BOYAmt>
        <EOYAmt>1835</EOYAmt>
      </OtherAssetsTotalDetail>
      <Form990TotalAssetsGrp>
        <BOYAmt>18887</BOYAmt>
        <EOYAmt>16289</EOYAmt>
      </Form990TotalAssetsGrp>
      <NetAssetsOrFundBalancesGrp>
        <BOYAmt>18887</BOYAmt>
        <EOYAmt>16289</EOYAmt>
      </NetAssetsOrFundBalancesGrp>
      <InfoInScheduleOPartIIIInd>X</InfoInScheduleOPartIIIInd>
      <PrimaryExemptPurposeTxt>BOATING SAFETY AND EDUCATION.</PrimaryExemptPurposeTxt>
      <ProgramSrvcAccomplishmentGrp>
        <DescriptionProgramSrvcAccomTxt>SAFE BOATING AND EDUCATIONAL CLASSES FOR MEMBERS AND THE GENERAL PUBLIC. VARIOUS CLASSES ARE HELD FOR NUMEROUS PARTICIPANTS OF THE GENERAL PUBLIC AND OTHER CLASSES ARE HELD FOR MEMBERS PARTICIPATING IN EDUCATING ELEMENTARY SCHOOL STUDENTS AS TO THE PROPER USE OF PERSONAL FLOATATION DEVICES. PARTICIPATED IN SAFE-BOATING WEEK ACTIVITIES. DISTRIBUTED NUMBEROUS SAFETY BOATING PACKETS. DEMONSTRATED PROPER USE OF FIRE EXTINGUISHERS AT THE MARINA AND PROPER USE OF THE PERSONAL FLOATATION DEVICES. DISTRIBUTED NUMEROUS SAFETY WHISTLES. OTHER ACTIVITIES FOR THE PROMOTION OF BOATING SAFETY.</DescriptionProgramSrvcAccomTxt>
        <ProgramServiceExpensesAmt>18769</ProgramServiceExpensesAmt>
      </ProgramSrvcAccomplishmentGrp>
      <TotalProgramServiceExpensesAmt>18769</TotalProgramServiceExpensesAmt>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>CHAD LOWNEY</PersonNm>
        <TitleTxt>COMMANDER</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>3.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>JASON YECOSHENKO</PersonNm>
        <TitleTxt>EXECUTIVE OF</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>3.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>STACEY LOWNEY</PersonNm>
        <TitleTxt>SECRETARY</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>3.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>LORI YECOSHENKO</PersonNm>
        <TitleTxt>TREASURER</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>3.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>GUY PARTCH</PersonNm>
        <TitleTxt>EDUCATION OF</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>3.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>DAVE CARLSON</PersonNm>
        <TitleTxt>MEMBER AT LA</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>3.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>DUANE FLYNN</PersonNm>
        <TitleTxt>MEMBER AT LA</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>3.00</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <ActivitiesNotPreviouslyRptInd>false</ActivitiesNotPreviouslyRptInd>
      <ChgMadeToOrgnzngDocNotRptInd>false</ChgMadeToOrgnzngDocNotRptInd>
      <OrganizationHadUBIInd>false</OrganizationHadUBIInd>
      <SubjectToProxyTaxInd>false</SubjectToProxyTaxInd>
      <OrganizationDissolvedEtcInd>false</OrganizationDissolvedEtcInd>
      <Form1120PolFiledInd>false</Form1120PolFiledInd>
      <MadeLoansToFromOfficersInd>false</MadeLoansToFromOfficersInd>
      <EngagedInExcessBenefitTransInd>false</EngagedInExcessBenefitTransInd>
      <ProhibitedTaxShelterTransInd>false</ProhibitedTaxShelterTransInd>
      <StatesWhereCopyOfReturnIsFldCd>MN</StatesWhereCopyOfReturnIsFldCd>
      <BooksInCareOfDetail>
        <PersonNm>LORI YECOSHENKO</PersonNm>
        <USAddress>
          <AddressLine1Txt>5797 WAHL ROAD</AddressLine1Txt>
          <CityNm>DULUTH</CityNm>
          <StateAbbreviationCd>MN</StateAbbreviationCd>
          <ZIPCd>55804</ZIPCd>
        </USAddress>
        <PhoneNum>2183494717</PhoneNum>
      </BooksInCareOfDetail>
      <ForeignFinancialAccountInd>false</ForeignFinancialAccountInd>
      <ForeignOfficeInd>false</ForeignOfficeInd>
      <DonorAdvisedFndsInd>false</DonorAdvisedFndsInd>
      <OperateHospitalInd>false</OperateHospitalInd>
      <TanningServicesProvidedInd>false</TanningServicesProvidedInd>
      <RelatedOrganizationCtrlEntInd>false</RelatedOrganizationCtrlEntInd>
      <TransactionWithControlEntInd>false</TransactionWithControlEntInd>
      <PoliticalCampaignActyInd>false</PoliticalCampaignActyInd>
      <LobbyingActivitiesInd>false</LobbyingActivitiesInd>
      <SchoolOperatingInd>false</SchoolOperatingInd>
      <TrnsfrExmptNonChrtblRltdOrgInd>false</TrnsfrExmptNonChrtblRltdOrgInd>
      <PartVIOfCompOfHghstPdEmplTxt>NONE</PartVIOfCompOfHghstPdEmplTxt>
      <PartVIHghstPdCntrctProfSrvcTxt>NONE</PartVIHghstPdCntrctProfSrvcTxt>
      <FiledScheduleAInd>true</FiledScheduleAInd>
    </IRS990EZ>
    <IRS990ScheduleA documentId="RetDoc4">
      <PubliclySupportedOrg509a2Ind>X</PubliclySupportedOrg509a2Ind>
      <GiftsGrantsContrisRcvd509Grp>
        <CurrentTaxYearMinus4YearsAmt>1096</CurrentTaxYearMinus4YearsAmt>
        <CurrentTaxYearMinus3YearsAmt>915</CurrentTaxYearMinus3YearsAmt>
        <CurrentTaxYearMinus2YearsAmt>1350</CurrentTaxYearMinus2YearsAmt>
        <CurrentTaxYearMinus1YearAmt>2294</CurrentTaxYearMinus1YearAmt>
        <CurrentTaxYearAmt>3651</CurrentTaxYearAmt>
        <TotalAmt>9306</TotalAmt>
      </GiftsGrantsContrisRcvd509Grp>
      <GrossReceiptsAdmissionsGrp>
        <CurrentTaxYearMinus4YearsAmt>5584</CurrentTaxYearMinus4YearsAmt>
        <CurrentTaxYearMinus3YearsAmt>5354</CurrentTaxYearMinus3YearsAmt>
        <CurrentTaxYearMinus2YearsAmt>36550</CurrentTaxYearMinus2YearsAmt>
        <CurrentTaxYearMinus1YearAmt>37385</CurrentTaxYearMinus1YearAmt>
        <CurrentTaxYearAmt>30263</CurrentTaxYearAmt>
        <TotalAmt>115136</TotalAmt>
      </GrossReceiptsAdmissionsGrp>
      <GrossReceiptsNonUnrltBusGrp>
        <CurrentTaxYearMinus4YearsAmt>23917</CurrentTaxYearMinus4YearsAmt>
        <CurrentTaxYearMinus3YearsAmt>20900</CurrentTaxYearMinus3YearsAmt>
        <TotalAmt>44817</TotalAmt>
      </GrossReceiptsNonUnrltBusGrp>
      <Total509Grp>
        <CurrentTaxYearMinus4YearsAmt>30597</CurrentTaxYearMinus4YearsAmt>
        <CurrentTaxYearMinus3YearsAmt>27169</CurrentTaxYearMinus3YearsAmt>
        <CurrentTaxYearMinus2YearsAmt>37900</CurrentTaxYearMinus2YearsAmt>
        <CurrentTaxYearMinus1YearAmt>39679</CurrentTaxYearMinus1YearAmt>
        <CurrentTaxYearAmt>33914</CurrentTaxYearAmt>
        <TotalAmt>169259</TotalAmt>
      </Total509Grp>
      <PublicSupportTotal509Amt>169259</PublicSupportTotal509Amt>
      <GrossInvestmentIncome509Grp>
        <CurrentTaxYearMinus4YearsAmt>11</CurrentTaxYearMinus4YearsAmt>
        <CurrentTaxYearMinus3YearsAmt>6</CurrentTaxYearMinus3YearsAmt>
        <CurrentTaxYearMinus2YearsAmt>3</CurrentTaxYearMinus2YearsAmt>
        <CurrentTaxYearMinus1YearAmt>3</CurrentTaxYearMinus1YearAmt>
        <CurrentTaxYearAmt>3</CurrentTaxYearAmt>
        <TotalAmt>26</TotalAmt>
      </GrossInvestmentIncome509Grp>
      <InvestmentIncomeAndUBTIGrp>
        <CurrentTaxYearMinus4YearsAmt>11</CurrentTaxYearMinus4YearsAmt>
        <CurrentTaxYearMinus3YearsAmt>6</CurrentTaxYearMinus3YearsAmt>
        <CurrentTaxYearMinus2YearsAmt>3</CurrentTaxYearMinus2YearsAmt>
        <CurrentTaxYearMinus1YearAmt>3</CurrentTaxYearMinus1YearAmt>
        <CurrentTaxYearAmt>3</CurrentTaxYearAmt>
        <TotalAmt>26</TotalAmt>
      </InvestmentIncomeAndUBTIGrp>
      <TotalSupportCalendarYearGrp>
        <CurrentTaxYearMinus4YearsAmt>30608</CurrentTaxYearMinus4YearsAmt>
        <CurrentTaxYearMinus3YearsAmt>27175</CurrentTaxYearMinus3YearsAmt>
        <CurrentTaxYearMinus2YearsAmt>37903</CurrentTaxYearMinus2YearsAmt>
        <CurrentTaxYearMinus1YearAmt>39682</CurrentTaxYearMinus1YearAmt>
        <CurrentTaxYearAmt>33917</CurrentTaxYearAmt>
        <TotalAmt>169285</TotalAmt>
      </TotalSupportCalendarYearGrp>
      <PublicSupportCY509Pct>0.99980</PublicSupportCY509Pct>
      <PublicSupportPY509Pct>0.99980</PublicSupportPY509Pct>
      <InvestmentIncomeCYPct>0.00000</InvestmentIncomeCYPct>
      <InvestmentIncomePYPct>0.00000</InvestmentIncomePYPct>
      <ThirtyThrPctSuprtTestsCY509Ind>X</ThirtyThrPctSuprtTestsCY509Ind>
    </IRS990ScheduleA>
    <IRS990ScheduleG documentId="RetDoc2">
      <FundraisingEventInformationGrp>
        <Event1Nm>FISHING CONTEST</Event1Nm>
        <GrossReceiptsEvent1Amt>8835</GrossReceiptsEvent1Amt>
        <GrossRevenueEvent1Amt>8835</GrossRevenueEvent1Amt>
        <OtherDirectExpensesEvent1Amt>3809</OtherDirectExpensesEvent1Amt>
        <Event2Nm>FITTING OUT PAR</Event2Nm>
        <GrossReceiptsEvent2Amt>6738</GrossReceiptsEvent2Amt>
        <GrossRevenueEvent2Amt>6738</GrossRevenueEvent2Amt>
        <OtherDirectExpensesEvent2Amt>2554</OtherDirectExpensesEvent2Amt>
        <OtherEventsTotalCnt>1</OtherEventsTotalCnt>
        <GrossReceiptsOtherEventsAmt>6162</GrossReceiptsOtherEventsAmt>
        <GrossRevenueOtherEventsAmt>6162</GrossRevenueOtherEventsAmt>
        <OthDirectExpnssOtherEventsAmt>6737</OthDirectExpnssOtherEventsAmt>
        <GrossReceiptsTotalAmt>21735</GrossReceiptsTotalAmt>
        <GrossRevenueTotalEventsAmt>21735</GrossRevenueTotalEventsAmt>
        <OthDirectExpnssTotalEventsAmt>13100</OthDirectExpnssTotalEventsAmt>
        <DirectExpenseSummaryEventsAmt>13100</DirectExpenseSummaryEventsAmt>
        <NetIncomeSummaryAmt>8635</NetIncomeSummaryAmt>
      </FundraisingEventInformationGrp>
    </IRS990ScheduleG>
    <IRS990ScheduleO documentId="RetDoc3">
      <SupplementalInformationDetail>
        <FormAndLineReferenceDesc>FORM 990-EZ, PART I, LINE 8</FormAndLineReferenceDesc>
        <ExplanationTxt>CHANGE OF WATCH 478 TOTAL 478</ExplanationTxt>
      </SupplementalInformationDetail>
      <SupplementalInformationDetail>
        <FormAndLineReferenceDesc>FORM 990-EZ, PART I, LINE 16</FormAndLineReferenceDesc>
        <ExplanationTxt>EXPENSES ADVERTISING AND PROMOTION 1,293 OFFICE 614 CONFERENCES/MEETINGS 1,581 CHANGE OF WATCH 1,120 EDUCATION 2,421 DUES 2,626 MEMBER ACTIVITIES 1,142 NON-INVESTMENT DEPRECIATION 105 TOTAL 10,902</ExplanationTxt>
      </SupplementalInformationDetail>
      <SupplementalInformationDetail>
        <FormAndLineReferenceDesc>FORM 990-EZ, PART II, LINE 24</FormAndLineReferenceDesc>
        <ExplanationTxt>ACCOUNTS RECEIVABLE 1,545 1,100 PREPAID EXPENSES AND DEFERRED CHARGES 600 630 FURNITURE AND EQUIPMENT 315 315 LESS ACCUMULATED DEPRECIATION 105 210 TOTAL 2,355 1,835</ExplanationTxt>
      </SupplementalInformationDetail>
      <SupplementalInformationDetail>
        <FormAndLineReferenceDesc>FORM 990-EZ, PART III, LINE 28</FormAndLineReferenceDesc>
        <ExplanationTxt>SAFE BOATING AND EDUCATIONAL CLASSES FOR MEMBERS AND THE GENERAL PUBLIC. VARIOUS CLASSES ARE HELD FOR NUMEROUS PARTICIPANTS OF THE GENERAL PUBLIC AND OTHER CLASSES ARE HELD FOR MEMBERS PARTICIPATING IN EDUCATING ELEMENTARY SCHOOL STUDENTS AS TO THE PROPER USE OF PERSONAL FLOATATION DEVICES. PARTICIPATED IN SAFE-BOATING WEEK ACTIVITIES. DISTRIBUTED NUMBEROUS SAFETY BOATING PACKETS. DEMONSTRATED PROPER USE OF FIRE EXTINGUISHERS AT THE MARINA AND PROPER USE OF THE PERSONAL FLOATATION DEVICES. DISTRIBUTED NUMEROUS SAFETY WHISTLES. OTHER ACTIVITIES FOR THE PROMOTION OF BOATING SAFETY.</ExplanationTxt>
      </SupplementalInformationDetail>
    </IRS990ScheduleO>
  </ReturnData>
</Return>