UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                    FORM 8-K

                                 CURRENT REPORT

                     Pursuant to Section 13 or 15(d) of the
                         Securities Exchange Act of 1934

                       Date of Report: September 13, 2005
                        (Date of earliest event reported)

                          21ST CENTURY HOLDING COMPANY
             (Exact name of registrant as specified in its charter)

            Florida                      0-2500111               65-0248866
-------------------------------  ------------------------  ---------------------
(State or other jurisdiction of  (Commission File Number)    (I.R.S. Employer
         incorporation)                                      Identification No.)

       3661 West Oakland Park Blvd., Suite 300
                Lauderdale Lakes, FL                           33311
------------------------------------------------------   ------------------
      (Address of principal executive offices)              (Zip Code)

       Registrant's telephone number, including area code: (954) 581-9993

                                 NOT APPLICABLE
          (Former Name or Former Address, if Changed Since Last Report)

Check the appropriate box below if the Form 8-K filing is intended to
simultaneously satisfy the filing obligation of the registrant under any of the
following provisions (see General Instruction A.2. below):

|_|   Written communications pursuant to Rule 425 under the Securities Act
      (17 CFR 230.425)

|_|   Soliciting material pursuant to Rule 14a-12 under the Exchange Act
      (17 CFR 240.14a-12)

|_|   Pre-commencement communications pursuant to Rule 14d-2(b) under the
      Exchange Act (17 CFR 240.14d-2(b))

|_|   Pre-commencement communications pursuant to Rule 13e-4(c) under the
      Exchange Act (17 CFR 240.13e-4(c))

<PAGE>

Item 7.01 Regulation FD Disclosure.

On September 13, 2005, 21st Century  Holding  Company (the  "Company")  issued a
press  release  to report  that its  subsidiary,  Federated  National  Insurance
Company,  had received  approximately  2,100 claims reported to date for damages
sustained in Florida from Hurricane  Katrina.  The Company  amended its earnings
guidance  to $2.40 per share for  calendar  year  2005 and  issued  guidance  of
approximately  $4.00 per  share  for  calendar  year  2006.  A copy of the press
release is  attached  to this  current  report on Form 8-K as  Exhibit  99.1 and
incorporated herein by reference.

Pursuant  to general  instruction  B.2 to Form 8-K,  the  information  furnished
pursuant to Item 7.01 shall not be deemed to be "filed" for  purposes of Section
18 of the Exchange Act or otherwise subject to the liabilities of that section.

Item 9.01 Financial Statements and Exhibits.

      (c) Exhibits.

      99.1 21st Century Holding Company Press Release, dated September 13, 2005.

<PAGE>

                                   SIGNATURES

Pursuant  to the  requirements  of the  Securities  Exchange  Act of  1934,  the
registrant  has duly  caused  this  report  to be  signed  on its  behalf by the
undersigned hereunto duly authorized.


                                        21ST CENTURY HOLDING COMPANY


Date: September 14, 2005                By:  /s/ Richard A. Widdicombe
                                            ------------------------------------
                                        Name:    Richard A. Widdicombe
                                        Title:   Chief Executive Officer
                                                (Principal Executive Officer)


Date: September 14, 2005                By:  /s/ James Gordon Jennings, III
                                            ------------------------------------
                                        Name:    James Gordon Jennings, III
                                        Title:   Chief Financial Officer
                                                (Principal Accounting and
                                                 Financial Officer)

<PAGE>

                                 EXHIBIT INDEX

Exhibit No.      Exhibit Title
-----------      --------------
99.1             21st Century Holding Company Press Release, dated
                 September 13, 2005.
{"company-data": {"conformed-name": "21ST CENTURY HOLDING CO", "cik": "0001069996", "assigned-sic": "6331", "irs-number": "650248866", "state-of-incorporation": "FL", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "8-K", "act": "34", "file-number": "000-25001", "film-number": "051084394"}, "business-address": {"street1": "3661 WEST OAKLAND PARK BLVD", "street2": "SUITE 300", "city": "LAUDERDALE LAKES", "state": "FL", "zip": "33311", "phone": "9545819993"}, "mail-address": {"street1": "3661 WEST OAKLAND PARK BLVD", "street2": "SUITE 300", "city": "LAUDERDALE LAKES", "state": "FL", "zip": "33311"}}
UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                    FORM 8-K

                                 CURRENT REPORT

                     Pursuant to Section 13 or 15(d) of the
                         Securities Exchange Act of 1934

                       Date of Report: September 13, 2005
                        (Date of earliest event reported)

                          21ST CENTURY HOLDING COMPANY
             (Exact name of registrant as specified in its charter)

            Florida                      0-2500111               65-0248866
-------------------------------  ------------------------  ---------------------
(State or other jurisdiction of  (Commission File Number)    (I.R.S. Employer
         incorporation)                                      Identification No.)

       3661 West Oakland Park Blvd., Suite 300
                Lauderdale Lakes, FL                           33311
------------------------------------------------------   ------------------
      (Address of principal executive offices)              (Zip Code)

       Registrant's telephone number, including area code: (954) 581-9993

                                 NOT APPLICABLE
          (Former Name or Former Address, if Changed Since Last Report)

Check the appropriate box below if the Form 8-K filing is intended to
simultaneously satisfy the filing obligation of the registrant under any of the
following provisions (see General Instruction A.2. below):

|_|   Written communications pursuant to Rule 425 under the Securities Act
      (17 CFR 230.425)

|_|   Soliciting material pursuant to Rule 14a-12 under the Exchange Act
      (17 CFR 240.14a-12)

|_|   Pre-commencement communications pursuant to Rule 14d-2(b) under the
      Exchange Act (17 CFR 240.14d-2(b))

|_|   Pre-commencement communications pursuant to Rule 13e-4(c) under the
      Exchange Act (17 CFR 240.13e-4(c))
Item 7.01 Regulation FD Disclosure.

On September 13, 2005, 21st Century  Holding  Company (the  "Company")  issued a
press  release  to report  that its  subsidiary,  Federated  National  Insurance
Company,  had received  approximately  2,100 claims reported to date for damages
sustained in Florida from Hurricane  Katrina.  The Company  amended its earnings
guidance  to $2.40 per share for  calendar  year  2005 and  issued  guidance  of
approximately  $4.00 per  share  for  calendar  year  2006.  A copy of the press
release is  attached  to this  current  report on Form 8-K as  Exhibit  99.1 and
incorporated herein by reference.

Pursuant  to general  instruction  B.2 to Form 8-K,  the  information  furnished
pursuant to Item 7.01 shall not be deemed to be "filed" for  purposes of Section
18 of the Exchange Act or otherwise subject to the liabilities of that section.

Item 9.01 Financial Statements and Exhibits.

      (c) Exhibits.

      99.1 21st Century Holding Company Press Release, dated September 13, 2005.
SIGNATURES

Pursuant  to the  requirements  of the  Securities  Exchange  Act of  1934,  the
registrant  has duly  caused  this  report  to be  signed  on its  behalf by the
undersigned hereunto duly authorized.

                                        21ST CENTURY HOLDING COMPANY

Date: September 14, 2005                By:  /s/ Richard A. Widdicombe
                                            ------------------------------------
                                        Name:    Richard A. Widdicombe
                                        Title:   Chief Executive Officer
                                                (Principal Executive Officer)

Date: September 14, 2005                By:  /s/ James Gordon Jennings, III
                                            ------------------------------------
                                        Name:    James Gordon Jennings, III
                                        Title:   Chief Financial Officer
                                                (Principal Accounting and
                                                 Financial Officer)
EXHIBIT INDEX

Exhibit No.      Exhibit Title
-----------      --------------
99.1             21st Century Holding Company Press Release, dated
                 September 13, 2005.