A couple of other observations springing from the research done for the "Hungry Like The Wolf" thread.
The Mighty That Have Fallen - Or Slipped A Bit
Woodrow Wilson
The hands-down, runaway winner of this category. Incredible as it now seems, the Presidents were a state power in the late eighties and early nineties. Wilson won AAA, Division 5 titles in '89 and '91. As the Wilson faithful celebrated on the field after the second of those championships, I doubt that any of them could have ever envisioned that that would be the last time their team would even sniff the playoffs. As a result, Wilson's all-time playoff record stands frozen at an excellent 14-7.
E. C. Glass
Glass was a long-time football big boy in the pre-playoff era. The Hilltoppers continued to thrive into the nineties, winning the Division 5 crown in '88, and finishing as runners-up in 1995. In the twenty seasons since, Glass has made only six playoff appearances, going a combined 1-6 in those trips.
Park View (Sterling)
The Patriots stormed to the 1988 Division 4 championship, and were state runners-up on three other occasions. Following the most recent of those in 2000, PV has a 4-8 playoff record, and has not visited the postseason since 2011.
Powhatan
Winners of titles in both Division 2 (1996) and Division 4 (2003), the Indians are mired in a four-game playoff losing skid, last notching a win in 2011.
Harrisonburg
Seemingly a perennial contender until the last decade, the Blue Streaks last made the post-season in 2011; their last playoff win came the previous season.
Handley
Though not atrocious, the Judges' 10-11 playoff record since finishing as Division 3 runners-up in '99 seems rather uninspired for a two-time state champion ('84 and '94). Handley hasn't tasted postseason victory since 2010.
Surprising Postseason Underachievers
These are schools whose lack of playoff success took me aback. Although there are many other schools with even worse resumes, I somehow thought these teams had fared better.
William Fleming
I knew Fleming hadn't been wildly successful in the postseason, but their all-time record of 8-16 still came as a surprise. And even that limited success is very narrow: Fleming has twice finished as runners-up, in '97 (Div. 5) and '03 (Div. 4). Aside from those two years, Fleming has a combined grand total of two playoff victories. None in the seventies, one in the eighties.
Charlottesville
The Knights' all-time playoff mark stands at 4-11. Only once have they ever won more than one playoff game in the same season.
Grafton
Being located in such a talent-rich area, I would have thought the Clippers would have managed to do better than 4-9 in their playoff trips. At least they paired those victories up nicely, reaching state semis in '04 and '11.
Smithfield
I'm not sure why exactly, but I found the Packers' dismal playoff record of 2-12 to be one of the biggest surprises. It just seems like I've heard about them forever; apparently, not for reasons related to football glory.
The Mighty That Have Fallen - Or Slipped A Bit
Woodrow Wilson
The hands-down, runaway winner of this category. Incredible as it now seems, the Presidents were a state power in the late eighties and early nineties. Wilson won AAA, Division 5 titles in '89 and '91. As the Wilson faithful celebrated on the field after the second of those championships, I doubt that any of them could have ever envisioned that that would be the last time their team would even sniff the playoffs. As a result, Wilson's all-time playoff record stands frozen at an excellent 14-7.
E. C. Glass
Glass was a long-time football big boy in the pre-playoff era. The Hilltoppers continued to thrive into the nineties, winning the Division 5 crown in '88, and finishing as runners-up in 1995. In the twenty seasons since, Glass has made only six playoff appearances, going a combined 1-6 in those trips.
Park View (Sterling)
The Patriots stormed to the 1988 Division 4 championship, and were state runners-up on three other occasions. Following the most recent of those in 2000, PV has a 4-8 playoff record, and has not visited the postseason since 2011.
Powhatan
Winners of titles in both Division 2 (1996) and Division 4 (2003), the Indians are mired in a four-game playoff losing skid, last notching a win in 2011.
Harrisonburg
Seemingly a perennial contender until the last decade, the Blue Streaks last made the post-season in 2011; their last playoff win came the previous season.
Handley
Though not atrocious, the Judges' 10-11 playoff record since finishing as Division 3 runners-up in '99 seems rather uninspired for a two-time state champion ('84 and '94). Handley hasn't tasted postseason victory since 2010.
Surprising Postseason Underachievers
These are schools whose lack of playoff success took me aback. Although there are many other schools with even worse resumes, I somehow thought these teams had fared better.
William Fleming
I knew Fleming hadn't been wildly successful in the postseason, but their all-time record of 8-16 still came as a surprise. And even that limited success is very narrow: Fleming has twice finished as runners-up, in '97 (Div. 5) and '03 (Div. 4). Aside from those two years, Fleming has a combined grand total of two playoff victories. None in the seventies, one in the eighties.
Charlottesville
The Knights' all-time playoff mark stands at 4-11. Only once have they ever won more than one playoff game in the same season.
Grafton
Being located in such a talent-rich area, I would have thought the Clippers would have managed to do better than 4-9 in their playoff trips. At least they paired those victories up nicely, reaching state semis in '04 and '11.
Smithfield
I'm not sure why exactly, but I found the Packers' dismal playoff record of 2-12 to be one of the biggest surprises. It just seems like I've heard about them forever; apparently, not for reasons related to football glory.