Exiting the 1990s Trimble had won 3 of the 6 TVC-Hocking Championships.  More than any other school, but without a venture into the state playoffs.  As the new millennium began, so did an expanded format for the OHSAA state football playoffs.  The new state playoffs would consist of eight teams per region which would create more postseason possibilities.  It also gave the top four seeds in each region the opportunity to host a first round playoff game.  In 2001 the Tomcats finished the regular season 9-1, and for the first time in school history, hosted a playoff game.  In a rematch of the TVC-Hocking Championship game, Trimble beat Eastern 23-6 for the Tomcat’s first ever playoff victory.  The Tomcats would go into the postseason 4 times in the decade and finish one spot out of playoff qualification twice.  

More importantly to most Trimble fans, 2001 would also feature a win over Nelsonville-York, the first in eleven seasons.  The Tomcat/Buckeye rivalry would revert back to the competitiveness of the late 70s and 80s.  Games with one score or one point differentials would amp up the intensity in what was already considered one of the greatest football rivalries in southeastern Ohio.  The 2005 game was the first time a Trimble/Nelsonville-York game went into overtime. In that game the ‘Cats held Nelsonville on a fourth and goal from the four yard line to hold the Buckeyes scoreless in the first overtime, Trent Nott scored the walk off TD on the second play of Trimble’s offensive possession.

As the decade came to a close, Trimble made an alteration to their offense.  In past years under Coach Faires, the Tomcats would switch to a double tight wing-T look in short yardage, or possibly into the Power I.  In 2008 the ‘Cats started to use the Wishbone.  As the season progressed, more and more plays came out of the Wishbone and this formation was competing to be the most used in the offensive playbook.  The last time a Trimble team consistently ran the Wishbone was the 1974 season, but beginning in 2008, it became a staple of the Tomcat offense once again.

Final Computer Rank: 15th Division VI Region 23

Post Season Awards:

All TVC Hocking: Kyle Andrews (Defensive Player of the Year) Kasey Dixon, Justin Guinther

All District: Adam Faires, Kyle Andrews, Justin Guinther

Team Members: Justin Guinther, Jesse Brunton, Jeff Trace, Trent Patton, Bobby Trace, Russell Guffey, Todd Williams, A.J. Jenkins, Mike Jago, Joe Cooper, Alex Shust, Justin Jenkins, Denver Shover, Dan Stier, Marc Skinner, Kyle Andrews, Phillip Vickers, Travis Nott, Zach Walton, Josh Shafer, Billy Ray, Larry Buchman, Earl Gilkey, Kasey Dixon, Mike Losey, Alan Lanning, Adam Faires, Kalum Dixon, Jason Leach, John Boudinot, Jason Smith, Billy Stevens, Travis McElfresh, Justin Hodgson

Assistant Coaches: Roger Bingman, Phil Campbell, Todd Trace, Donny Holbert, Rusty Martin Greg Koons

Managers: Hannah Faires, Julie Trace, Jeremiah Couch

The Eastern playoff game was the first playoff win in school history.  The Danville game was played at Newark White Field.

Final Computer Rank: 2nd Division VI Region 23

Post Season Awards:

All TVC Hocking: Kyle Andrews (Defensive Player of the Year) Jesse Brunton, Adam Faires, Dave Lanning, Travis Nott, Bobby Trace, Jeff Trace, Phil Faires (Coach of the Year)

All District: Kyle Andrews (Defensive Player of the Year), Jeff Trace, Travis Nott, Adam Faires, Bobby Trace, Alex Shust, Phil Faires (Coach of the Year) 

All Ohio: First Team - Kyle Andrews 

Team Members (Numerically) #1 Bobby Trace, #5 Jesse Brunton, #7 Justin Hodgson, #8 Jeff Trace, #10 Robby Jenkins, #11 Jeff Weaver, #12 Zach Shust, #15 Jonah McClelland, #20 Nathan Hill, #22 Todd Williams, #24 Tory Smith, #25 A.J. Jenkins, #30 Mike Jago, #32 Joe Cooper, #33 Alex Shust, #34 Justin Jenkins, #36 Steve Hartley, #40 Dan Stier, #41 R.J. Andrews, #42 Marc Skinner, #45 Kyle Andrews, #50 Phillip Vickers, #51 Travis Nott, #52 Derek Liskey, #54 Jason Leach, #55 Bruce Fouts, #56 Dave Lanning, #57 Billy Ray, #58 Larry Buchman, #60 Erich Vess, #61 Kalum Dixon, #62 Mike Losey, #64 Alan Lanning, #65 Adam Faires, #66 Zach Walton, #67 Colt Handa, #68 Michael Harper, #70 Zack Jenkins, #71 Jason Smith, #72 Brandon Hogsett, #74 Corey Sikorski, #80 Travis McElfresh, #81 Cody Handa, #86 Chaz Duncan

The Portsmouth Notre Dame game was called at halftime due to weather conditions.

Final Computer Rank: 9th Division VI Region 23

Post Season Awards:

All TVC Hocking: A.J. Jenkins (Defensive Player of the Year) R.J. Andrews, Alan Lanning, Zach Walton, Bruce Fouts

All District: R.J. Andrews, A.J. Jenkins, Alan Lanning, Bruce Fouts

The Fisher Catholic game was played at Fairfield Union high school.

A.J. Jenkins becomes the first Tomcat Quarterback to throw for over 2,000 yards in a season, finishing with 2,177 yards

Final Computer Rank: 6th Division VI Region 23

Post Season Awards:

All TVC Hocking: A.J. Jenkins (Offensive Player of the Year) Bruce Fouts (Defensive Player of the Year) Justin Jenkins, Travis McElfresh, Mike Harper, Steven Hartley, Robby Jenkins

All District: A.J. Jenkins (Offensive Player of the Year), Mike Harper, Robby Jenkins, Bruce Fouts, Phil Faires (Coach of the Year)

All Ohio: First Team - A.J. Jenkins 

Due to Glouster Memorial Stadium being flooded, the Wahama game was played at Ohio University’s Peden Stadium

Final Computer Rank: 4th Division VI Region 23

Post Season Awards:

All TVC Hocking: Robby Jenkins (Offensive Player of the Year) Bruce Fouts (Defensive Player of the Year), Mike Harper, Terry Holbert, Zach Shust, Derek Liskey

All District: Robby Jenkins (Offensive Player of the Year) Bruce Fouts (Defensive Player of the Year), Zach Shust, Mike Harper, Terry Holbert, Derek Liskey, Phil Faires (Coach of the Year) 

All Ohio: First Team - Robby Jenkins, Bruce Fouts, Second Team - Mike Harper 

Final Computer Rank: 9th Division V Region 19

Post Season Awards: 

All TVC Hocking: Mark Christman (Defensive Player of the Year), Anthony Dixon, Brett Flowers, Trent Nott, B. Barrett

All District: Mark Christman (Defensive Player of the Year), Anthony Dixon, B. Barrett, Brett Flowers

All Ohio: First Team - Mark Christman, Second Team - Anthony Dixon

Team Members: Joe Eing, Isaac Standley, Blake Fouts, Trent Nott, Cory Morgan, Anthony Dixon, Kacey Cruse, Chris Runyon, Chaz Mohler, Brad Russell, Derek Banik, Taylor Russell, Brian Foughty, Matt Christman, Robert “B” Barrett, Lance Bonham, Kevin Simons, Joe Dixon, Scott Bycofski, Zach Cox, Ryan Nagucki, Mark Christman, Chuck Dunlevy, James Simonis, Charles Faires, Josh McCoy, Kenny Verkest, Nick Giffin, Brandon Webster, Cody Jago, Tony Troiano, Brett Flowers, Michael Moleski, Tony Miller, Josh Dixon, Warren Smith, Randy Waldeck, Homer Dillon, Dave Clark, Derek Gyure, Brandon Keith, Joseph Craig

Assistant Coaches: Donny Holbert, Phil Campbell, Scott Christman, Phillip Faires, Adam Faires, Dennis Osborne, Rusty Richards, Greg Koons

Final Computer Rank: 16th Division V Region 19

Post Season Awards: 

All TVC Hocking: Blake Fouts (Offensive Player of the Year), Mark Christman, Scott Bycofski, Isaac Standley, Joe Eing

All District: Blake Fouts, Charles Faires, Mark Christman, Isaac Standley

All Ohio: Second Team - Mark Christman

Team Members: Joe Eing, Isaac Standley, Blake Fouts, Roger Dyer, Nick Eing, Brad Russell, Mark Christman, Kacey Cruse, Chris Runyon, Adam Mulford, Andy Boysen, Corey Smathers, Brandon Carter, Richard Drake, Scott Bycofski, Zach Cox, Keifer Standley, Chuck Dunlevy, James Simonis, Charles Faires, Jamie Thompson, Brandon Brooks, Casey Martin, Jeremiah Borgen, Greg Keith, Brandon Keith, Michael Moleski, Rodney Davidson, Andrew McLaughlin, Benny Spears, Mathew Azbell, Dave Clark, Tyler Barrett, Derek Brown, Chaz Craig

Assistant Coaches: Phil Campbell, Scott Christman, Adam Faires, Phillip Faires, Tommy Hardy, Donny Holbert, Dennis Osborne, Rusty Richards, Todd Trace

Managers: Abby Bond, Danielle Dolan, Austin Downs, Brett Downs

Final Computer Rank: 12th Division VI Region 23

Post Season Awards:

All TVC Hocking: Scott Bycofski (Defensive Player of the Year), Charles Faires, Brandon Keith, Keifer Standley, Isaac Standley

All District: Isaac Standley, Joe Eing, Kacey Cruse, Charles Faires, Scott Bycofski

All Ohio: First Team - Charles Faires 

The River playoff game was played at Marietta’s Don Drumm Stadium.

Final Computer Rank: 4th Division VI Region 23

Post Season Awards:

All TVC Hocking: Tyler Dyla (Offensive Player of the Year), Keifer Standley (Defensive Player of the Year) Kacey Cruse, Kyle Dyer, Joe Eing, Brandon Keith, Adam Mulford

All District: Tyler Dyla (Offensive Player of the Year) Kacey Cruse, Adam Mulford, Kyle Dyer 

All Ohio: First Team - Tyler Dyla

Team Members: Joe Eing, Derek Banik, Brandon Keith, Adam Mulford, Kacey Cruse, Chris Runyon, Jeremiah Borgen, Matt Azbell, Brandon Carter, Casey Martin, Nick Eing, Coltan Joyce, Kiefer Standley, Roger Dyer, Richard Drake, Carl Williams, Johnny Stobart, Sonny Cain, Tyler Dyla, Eric Putnam, Kendall Herbert, Charles Kish, Cyrus Jones, J.D. Chesser, Braiden Bickley, Tommy Palmer, Mitch Miller, Storm Rushing, Chris Spears, B.J. Whiteford, Jacob Hooper, Chad Smith, Austin Keith, Brandon Auflick, Noah Guthrie, Andrew McLaughlin, Justin Jewell, Brandon Riley, Charles Hardy

Assistant Coaches: Curt Moore, Rusty Richards, Phil Campbell, Dennis Osborne, Don Holbert

Managers: Nathan Downs, Anthony McLaughlin

Final Computer Rank: 12th Division VI Region 23

Post Season Awards:

All TVC Hocking: Tyler Dyla (Offensive Player of the Year), Kiefer Standley (Defensive Player of the Year), Richard Drake, Roger Dyer, Nick Eing, Andrew McLaughlin, Johnny Stobart

All District: Tyler Dyla (Offensive Player of the Year) Andrew McLaughlin, Kiefer Standley, Johnny Stobart

All Ohio: First Team - Tyler Dyla