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8-1999 Shifty

8-14-1999 "Sherriff" Johnny Emerald (St. Paul, MN)

1999 VACATED

1-28-2000 CM Punk (1) (West St. Paul, MN)

-Defeated Black Dagger in a tournament final for the vacant title.

6-3-2000 Derek St. Holmes, Esq. (West St. Paul, MN)

9-22-2000 "Sexy" Ace Steel (West St. Paul, MN)

4-27-2001 Jerry Lynn (West St. Paul, MN)

4-27-2001 VACATED

-Jerry Lynn surrendered the title after winning it because he was leaving SDW for the WWF.

4-28-2001 CM Punk (2) (West St. Paul, MN)

-Defeated Ace Steel in a ladder match for the vacant title.

12-29-2001 "Classic" Colt Cabana (West St. Paul, MN)

12-29-2001 Magnus Maximus (West St. Paul, MN)

-After winning the title, Colt Cabana sold the championship to manager Mortimer Plumtree, who awarded the title to his client, Magnus Maximus.

12-29-2001 Horace The Psychopath (West St. Paul, MN)

4-27-2002 Adrian Lynch (West St. Paul, MN)

9-14-2002 Mitch Paradise (Red Wing, MN)

11-23-2002 Tracy Smothers (West St. Paul, MN)

4-26-2003 VACATED

-Tracy Smothers was stripped of the title for failure to defend.

4-26-2003 "The Natural" Matt Burns (West St. Paul, MN)

-Defeated "Wild" Bill Irwin for the vacant title.

5-2003 VACATED

5-31-2003 "Livewire" Johnny Parks (West St. Paul, MN)

-Defeated "Kamikaze" Ken Anderson for the vacant title.

9-26-2003 Gage Octane (Savage, MN)

3-21-2004 Pretty Boy Delgado (Maple Grove, MN)

6-?-2004 Tony DeNucci