BANNER PHOTO: Jason Palmer’s race team has won Pit Crew of the Year 6 times between the Legend Car and Late Model divisions (DMS photo)
KEY: ?? = we have yet to verify the recipient of the award OR verify if the award was actually presented by Speedbowl officals. Please CONTACT US if you have information on the missing recipients
| YEAR | SK MODIFIED | LATE MODEL | SPORTSMAN | MINI STOCK | SAT LEGEND CAR | ||||||
| 1995 | Dave Gada | Phil Rondeau | Ernie LaRose | Brandon Plemons | |||||||
| 1996 | Dennis Gada | Phil Rondeau | Scott Cook | Bruce Thomas | |||||||
| 1997 | Mark LaJeunesse | Matt Kobyluck | Dan Darnstaedt | Billy Guyette | |||||||
| 1998 | Harry Rheaume | Jeff Karns | Ed Gertsch Jr | Roger Perry | |||||||
| 1999 | Dennis Gada | Phil Rondeau | Phil Smith | Bud Hartson | |||||||
| 2000 | Jerry Pearl | Phil Rondeau | Monahan Racing A | Jeff Miller | |||||||
| 2001 | Ed Reed Jr | Corey Hutchings | Norm Root Jr | Dave Trudeau | |||||||
| 2002 | Don Fowler | Larry Goss | Walt Hovey Jr | Danny Field | not awarded | ||||||
| 2003 | Ed Reed Jr | Mark St. Hilaire | Sean Curtis | Wayne Burroughs Jr | not awarded | ||||||
| 2004 | Jeff Pearl | Carl Erickson | Norm Root Jr | Tim Jordan | George Whitney | ||||||
| 2005 | Tom Fox | Mark St. Hilaire | Norm Root Jr | Bill Leonard | Esposito Racing B | ||||||
| 2006 | Wendell Dailey | Jay Lozyniak | Ed Giles | Joe Godbout III | Jason Palmer | ||||||
| 2007 | Jeff Pearl | Mike Sangermano C | Jack Aquilina | Phil Evans | Justin Rau | ||||||
| 2008 | Keith Rocco | Bruce Thomas Jr | Ed Lamb Jr | Ken Cassidy Jr | Jason Palmer | WED LEGEND CAR | SK LIGHT | SUPER X-CAR | X-CAR | TRUCK | BANDOLERO |
| 2009 | Ron Yuhas Jr | Vin Esposito | Ed Puleo | Ian Brew | Jason Palmer | not awarded | not awarded | not awarded | not awarded | Howard Payne | not awarded |
| 2010 | Keith Rocco | Rich Staskowski | Greg Moran Jr | Ian Brew | Anthony Flannery | not awarded | not awarded | not awarded | not awarded | Scott Gregory | not awarded |
| 2011 | Tyler Chadwick | Jeff Smith | Ed Puleo | Ken Cassidy Jr | Dana DiMatteo | not awarded | Chris Correll | not awarded | not awarded | not awarded | |
| 2012 | Rob Janovic Jr | Dillon Moltz | Dan Darnstaedt | Ray Christian III | Dylan Izzo | not awarded | Paul French | not awarded | not awarded | not awarded | |
| 2013 | Kyle James | Jason Palmer | Josh Galvin | Garrett Denton | Giovanni Giarratana | Mike Christopher Jr | Randy Churchill Jr | Mike Maskell II | John Bowes | Morin Racing D | |
| 2014 | Craig Lutz | Bruce Thomas Jr | Phil Evans | Wayne Burroughs Jr | Scott Limkemann | Scott Limkemann | Randy Churchill Jr | Kevin Moon | Mitch Bombard | Anthony Marvin | |
| 2015 | Ted Christopher | Jason Palmer | Corey Coates | Wayne Burroughs Jr | Noah Korner | ?? | Corey Barry | Brian Norman | ?? | ?? | |
| 2016 | Dennis Perry | Keith Rocco | Chris Meyer | Jacob Perry | Dana DiMatteo | Noah Korner | Tony Membrino Jr | Bill Reiman | Kyle Gero | Josh Stringer | Tyler Barry |
| 2017 | Kyle James | Anthony Flannery | Al Stone III | Sean Caron | Jonathon Puleo | not awarded | Dana DiMatteo | not awarded | not awarded | Todd Taylor | not awarded |
| 2018 | Todd Owen | Jason Palmer | Jordan Hadley | Doug Curry | Corey Caddick | Jencik Family | not awarded | Marc Shafer | Dylan DeCoster | Duane Noll | Jencik Family |
| 2019 | track closed | ||||||||||
| 2020 | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded |
| 2021 | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded |
| 2022 | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded | not awarded |
A awarded to race team of brothers Shawn & Diego Monahan
B awarded to race team of brothers Vin & Mark Esposito
C awarded to car owner Mike Sangermano – #90 driven by Allen Coates, Tom Fox & Ron Yuhas Jr during the season
D awarded to race team of brothers Ken Jr & Andrew Morin