In 1997, Rob Castleman and a small group of players from southern Oregon created the Douglas Outlaws and competed as a independent team against Pacific Football League 'North' Division teams. At the same time, another Oregon team called the Southern Oregon Timberwolves played the same type of independent schedule in the PFL South (Northern California).  The season finale trip up to Edmonds, Washington was cancelled due to a lack of players available to make the long trip north.

At the conclusion of that year, both teams decided Oregon needed its own league. Although the Outlaws remained the same, the Timberwolves broke up with players from the 'Wolves forming 3 separate teams; the Rogue Warriors, the Rogue Valley Blaze (both from Medford), and the Klamath County Crusaders (Klamath Falls).  The Oregon Football League was officially born.  Douglas County finished with an overal 1-6 record for the 1998 season.

In 1999 and 2000, the Douglas Outlaws showed a little improvement, but so did the rest of the OFL. Hence, the Outlaws finished both seasons 2-6 and 1-6 respectively.  Aaron Bayer set a league and regional interception record when he picked off 15 passes in 1999 including four in one game against the Rogue Warriors.  Bayer earned Oregon Football League Defensive MVP honors and Greater Northwest Player of the Year.

In 2001, the OFL saw perennial powerhouse Rogue Warriors roster decimated by a local arena league pro team.  For the first time in their five year history, the Douglas Outlaws won their season opener by shutting out the Central Oregon Stampede 14-0, Saturday night at Douglas High School.

Fullback Heath Wharton led the way with two rushing touchdowns and Tailback Micah Floth gained 87 yards on 15 carries against the Stampede. Wingback Gene Kailiuli led the receiving corps catching two passes for 22 yards.  Inside Linebackers Mike Nores and Willie James led the way, with nine and eight tackles respectively. Safeties Gene Kailiuli and Mike Jackson each had an interception, as the defense forced six turnovers. Nose Guard Eric Koegler had three-and-a-half sacks and recovered a fumble and Outside Linebacker Rob Castleman had two sacks, forced a fumble and had a fumble recovery.  Keith Fuchs sparked the special teams by averaging 41.3 yards per punt and 30 yards per punt return.  Heath Wharton would go on to be a key cog in the formation of the Oregon Monarchs from 2006 - 2013 which produced a dynasty of Oregon and Pacific League championships in 2008, 2009, 2010, 2012 and winning the GNFA Regional title three times in 2009, 2010 and 2012.

 In a game filled with mistakes, injuries and turnovers the Douglas Outlaws finished the regular season 3-3, losing to the Klamath County Crusaders 25-6 last Saturday night at Douglas High School.  Quarterback Scott Aker completed 10 passes for 140 yards, with one touchdown and four interceptions. Keith Fuchs had three catches for 64 yards, and finished the game with 123-all purpose yards.  The defense was led by inside linebacker Heath Wharton’s 12 tackles. Outside linebacker Brian Benavente had nine tackles, one for loss, forced a fumble and recovered a fumble while strong safety Rob Castleman had eight tackles and broke up four passes. 

Although the Outlaws finished tied for second place in the regular season, a league ruling that Rogue used "professional" players from the indoor team resulted in a prior Outlaw loss being ruled a forfeit win and the Warriors were expelled from the championship chase.  The door opened for the Outlaws who defeated Klamath 3-2  in a defensive battle without the services of linebacker Willie James and Rob Castleman who were lost to injury after the regular season finale.  Douglas County would finish the OFL season 4-3 for the Outlaws' first and only Oregon League championship.  The following week, in his first start at tailback, running behind an injured and revamped offensive line, Brian Marsters ran for 114-yards and one touchdown on 21 carries, but it wasn’t enough as the ”AA” Outlaws fell to the “AAA” Willamette Valley Raiders 26-12.  The Outlaws played the game with only 14 players.  The Raiders would go on to finish 6-1 the only loss to Portland's Multnomah County Buccaneers, Northwest League champions, and NFA West Coast runners-up with a 12-2 record.

Fullback Heath Wharton tallied 67-yards rushing on eight carries, while Keith Fuchs had two catches for 50 yards and Bion Mills added 31 yards receiving and a touchdown catch on four receptions. Quarterback Scott Aker completed seven of 15 passes for 101 yards, with four interceptions and one touchdown.  Safety Rocky Rodgers paced the defense with two interceptions. Cornerbacks Ryan Thomason and Keith Fuchs each had one interception, and Thomason also pitched in with six tackles, as did linebackers Brian Benavente and Eric Koegler.

The Outlaws, (4-2) in league play and (4-3) overall, finished the season as OFL Champions and ranked 18th in the nation according to Minor League Football News. 

  Preparing for Title Defense

The 2002 season would be the last for the Outlaws in Douglas County going 1-7 on the year. After the disappointing season, the Outlaws changed locations setting up camp in Coos Bay, Oregon, where groundwork had been laid at the end of 2001 with the game against the Raiders. Changing their name from the Douglas Outlaws to the Southwestern Oregon Raiders, the move opened the door for the Umpqua Valley Knights to set up shop in Roseburg under Bion Mills, two-time Outlaw All-League selection (2000, 2001). 

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