Format: Expanded 8-team playoff bracket (single-elimination quarterfinals, best-of-3 semis & finals).
Result: Charlottesville Tom Sox won the Valley League Championship (4th title)!
| Round | Opponent | Score | Location | Notes |
|---|---|---|---|---|
| Quarterfinal | Front Royal (8) | W 9-2 | Home | Advanced to Semis |
| Semifinal | Waynesboro (5) | W 4-1 | Home | |
| Championship G1 | Pulaski (2) | W 10-3 | Home | Best-of-3 |
| Championship G2 | @ Pulaski | W 7-4 | Away | Clinched Title |
- Series Outcome: Tom Sox sweep Pulaski in Finals, 2-0
- Key Highlight: Fourth VBL Championship in team history
- 2024 Champions
Format: Top 8 teams, best-of-3 all rounds.
Result: Charlottesville Tom Sox – VBL Runner-Up (Lost in Finals)
| Round | Opponent | Score | Location | Notes |
|---|---|---|---|---|
| Quarterfinals G1 | Front Royal | L 6-17 | Home | |
| Quarterfinals G2 | @ Front Royal | W 11-1 | Away | |
| Quarterfinals G3 | Front Royal | W 4-2 | Home | Advanced to Semis |
| Semifinals G1 | Strasburg | L 6-8 | Home | |
| Semifinals G2 | @ Strasburg | W 11-9 (10) | Away | |
| Semifinals G3 | Strasburg | W 6-3 | Home | Advanced to Finals |
| Finals G1 | Harrisonburg | L 2-7 | Home | |
| Finals G2 | @ Harrisonburg | L 5-9 | Away | Season ends |
- Series Outcome: Lost to Harrisonburg in Finals, 0-2
- Key Highlight: Back-to-back Finals appearances
Format: Top 8, best-of-3 quarterfinals, semifinals, and finals.
Result: Charlottesville Tom Sox win third VBL Championship!
| Round | Opponent | Score | Location | Notes |
|---|---|---|---|---|
| Quarterfinals G1 | Culpeper | L 1-4 | Home | |
| Quarterfinals G2 | @ Culpeper | W 8-1 | Away | |
| Quarterfinals G3 | Culpeper | W 19-2 | Home | Advanced to Semis |
| Semifinals G1 | Pulaski | W 7-5 (10) | Home | |
| Semifinals G2 | @ Pulaski | L 8-21 (7) | Away | |
| Semifinals G3 | Pulaski | W 9-5 | Home | Advanced to Finals |
| Finals G1 | Strasburg | W 6-3 | Home | Best-of-3 |
| Finals G2 | @ Strasburg | W 4-2 | Away | Clinched Title |
- Series Outcome: Tom Sox sweep Strasburg in Finals, 2-0
- Key Highlight: Third VBL Championship in team history
- 2022 Champions
Format: Top 4 in division, best-of-3 all rounds.
Result: Lost in first round
| Round | Opponent | Score | Location | Notes |
|---|---|---|---|---|
| Semifinals G1 | Waynesboro | L 1-3 | Home | |
| Semifinals G2 | @ Waynesboro | L 3-6 | Away | Eliminated |
- Series Outcome: Lost series 0-2
Format: South semifinals, South finals, best-of-3 league championship.
Result: Charlottesville Tom Sox win second VBL Championship!
| Round | Opponent | Score | Location | Notes |
|---|---|---|---|---|
| South Semifinals G1 | Waynesboro | L 1-3 | Home | |
| South Semifinals G2 | @ Waynesboro | L 3-6 | Away | Eliminated |
- Series Outcome: Eliminated in South Semifinals
- 2019 Championship series details to be inserted (see PDF for yearly records)
- 2019 Champions
Format: South semifinals, South finals, best-of-3 league championship.
Result: Charlottesville Tom Sox – VBL Runner-Up (Lost in Finals)
| Round | Opponent | Score | Location | Notes |
|---|---|---|---|---|
| South Semifinals G1 | Covington | W 9-4 | Home | |
| South Semifinals G2 | @ Covington | L 9-12 | Away | |
| South Semifinals G3 | Covington | W 10-5 | Home | Advanced to South Finals |
| South Finals G1 | Staunton | L 1-3 | Home | |
| South Finals G2 | @ Staunton | W 9-7 (10) | Away | |
| South Finals G3 | Staunton | W 10-2 | Home | Advanced to VBL Finals |
| VBL Finals G1 | @ Strasburg | W 11-8 | Away | Best-of-3 |
| VBL Finals G2 | Strasburg | W 4-1 | Home | Clinched Title |
- Series Outcome: Tom Sox win South, fall in Finals
- Key Highlight: Second straight Finals appearance
Format: South semifinals, South finals, best-of-3 league championship.
Result: Charlottesville Tom Sox win first VBL Championship!
| Round | Opponent | Score | Location | Notes |
|---|---|---|---|---|
| South Semifinals G1 | Staunton | W 11-2 | Home | |
| South Semifinals G2 | @ Staunton | W 10-5 | Away | Advanced to South Finals |
| South Finals G1 | Waynesboro | W 7-2 | Home | |
| South Finals G2 | @ Waynesboro | W 3-2 | Away | Clinched South Title |
| Championship G1 | Strasburg | L 7-9 | Home | Best-of-3 |
| Championship G2 | @ Strasburg | W 11-5 | Away | |
| Championship G3 | Strasburg | W 2-1 | Home | Clinched Title |
- Series Outcome: Tom Sox win Finals, 2-1 over Strasburg
- 2017 Champions
Format: Single play-in for final postseason spot.
Result: Lost in Play-In
| Round | Opponent | Score | Location | Notes |
|---|---|---|---|---|
| Play-In | @ Covington | L 5-6 | Away | Eliminated |
- Key Highlight: First-ever postseason appearance