November 27, 1975: Planning commenced on a "Minor league" diamond as a Memorial Project by the Royal Canadian Legion Branch # 43 to commemorate the 50th Anniversary of the Legion. Legion Diamond at Lakeview Park was officially opened on July 21, 1976. The project cost was $34,834.00 for lighting and poles, plus $8,842.50 for fencing. A "Wintario" Grant from the Ontario Government for $21,000 was also received.

Spring 2003: The Oshawa Legion (Minor) Baseball Association's official website came online for the first time on the "World Wide Web" to showcase the league, all its teams, and its members. The website address is www.baseballoshawa.com.

Spring 2004: The Oshawa Legion (Minor) Baseball Association applied to the "Ontario Trillium Foundation" to receive a grant to update Kinsmen Civic Memorial Stadium. Upgrades included a complete sprinkler system for the infield and outfield, new stadium grooming equipment, upgraded bullpens, outfield levelling, and permanent and maintenance-free foul lines.

On May 11, 2004, the OLMBA received $74,400 from the Ontario Trillium Foundation for this initiative. Ceremonies were held before the beginning of the Junior Legionnaires games. Dignitaries included Oshawa Mayor John Gray and M.P.P. Jerry Ouellette, who were on hand to throw out the first pitch before the scheduled Oshawa Legionnaire's game.

Spring 2004: Long-time Executive Member of the Oshawa Legion (Minor) Baseball Association Ted McComb is inducted into the Oshawa Sports Hall of Fame under the "Builders" category. The ceremony was held with many dignitaries and guests at the Oshawa Civic Auditorium. A framed picture of "Mr. Baseball" and his lifetime sports achievements are displayed at the Civic Arena Complex.

Spring 2005: Long-time Executive Member of the Oshawa Legion (Minor) Baseball Association Gladys Cochrane passed away. Many Legion Branch #43 and OLMBA friends and family attend funeral services and a reception. The OLMBA Executive unanimously votes to change the name of its annual golf tournament to the "Gladys Cochrane Memorial Golf Tournament." A trophy in Gladys' name will be awarded to the Mosquito Legionnaire "Most Valuable Player" each year. Further, the snack bar at Kinsmen Civic Memorial Stadium will be named the Gladys Cochrane Memorial Snack Bar.

Winter 2006: Long-time friend of the Oshawa Legion (Minor) Baseball Association and the Royal Canadian Legion Branch #43 and wife of OLMBA Executive Member Ted McComb passed away. Many Legion Branch #43 and OLMBA friends and family attend funeral services and a reception. She will be sadly missed.

Summer 2006: OLMBA, EOBA and Oshawa Dodger President Troy May passed away on Wednesday, July 19, 2006, due to injuries sustained in a car accident with his family on Sunday, July 16, 2006. Troy was instrumental in obtaining the OLMBA's first "Trillium Grant" from the Ontario Government. Upgrades from this grant included a sprinkler system for Kinsmen Stadium and other stadium equipment. Troy's love for the game and the youth of Oshawa will be sadly missed. Of note, the "Troy May Umpires Award," given each year to the OLMBA Senior Umpire of the Year, will be re-named the "Troy May Memorial Umpires Award," and subsequently, the annual Mosquito tournament will be re-named the "Troy May Memorial Mosquito Tournament."

Summer 2010. The Oshawa Legion Minor Baseball Association (OLMBA) hit a home run today with the newly renovated Kinsmen Stadium, made possible with a $101,000 grant from the Ontario Trillium Foundation (OTF). Jerry Ouellette, MPP for Oshawa, joined OTF representative John Stafford and Mayor John Gray in congratulating the Oshawa Legion Minor Baseball Executive at the ribbon-cutting ceremony. "Being actively involved in youth sports in our community, I can personally appreciate the importance of this OTF grant and the impact it will have on kids' recreation," said MPP Jerry Ouellette. "I wish to congratulate the many outstanding coaches and volunteers from the Oshawa Legion Minor Baseball Association on your recent grant from the Ontario Trillium Foundation to upgrade Kinsmen Stadium and continue to promote and enhance baseball in Oshawa." The OTF grants were used to replace the backstop, renovate the buildings, extend fencing and provide a canopy over the dugouts. Funding also supported OLMBA in purchasing pitching machines for the Rookie Ball division to help and improve training for local youth. "This grant will enhance the game of baseball in Oshawa," said Ryan McBride, President of OLMBA. "We are thankful for the Ontario Trillium Foundation's commitment to promoting physical activity in Ontario."

Established in 1949, the Oshawa Legion Minor Baseball Association provides a house league and Rep baseball program for children ages 4 to 18. The pitching machines for the Rookie ball teams have enhanced the quality of the game and improved the player's skill development. The OLMBA is volunteer-led and has successfully increased the number of registrations for the 2010 season. Baseball Oshawa board members Jane Norris and Dave Sheridan played a significant role in writing and submitting the successful Trillium Grant.

A leading grantmaker in Canada, the Ontario Trillium Foundation strengthens the capacity of the voluntary sector through investments in community-based initiatives. An agency of the Government of Ontario, OTF builds healthy and vibrant communities.

Summer 2014-16. Baseball Oshawa (OLMBA) was awarded the EOBA "Association of the Year" for three consecutive years. This special award recognized the outstanding contributions made by a dedicated Baseball Oshawa board and volunteers. While registrations continued to climb to new heights in Oshawa, the association delivered terrific experiences for its players through events like Baseball Day in Oshawa, Military Appreciation Week, and MLB Pitch HIt and Run events. While simultaneously hosting numerous EOBA and OBA Championship tournaments, including multiple-year hosts for the OBA Ontario Junor Elims Tourney. Baseball Oshawa also hosted EOBA special events such as the Mosquito and Peewee EOBA All-Star Games. Baseball Oshawa would be named EOBA Association of the year again in 2019 while finishing a close runner-up in 2021

Fall 2017. Jim Lutton, a Lifetime member of Baseball Oshawa OLMBA for his contributions to the game of baseball in Ontario for more than 60 years, was inducted into the Baseball Ontario Hall of Fame.

Summer 2018 and 2019. Baseball Oshawa successfully secured the 2-year bid to host the Baseball Canada 15U National Championship. Known as the Ray Carter Cup, it was the first time Baseball Oshawa OLMBA had hosted a National Championship in its more than 70-year history. The events were led by 15U Nationals Chairperson Ken Babcock (Baseball Oshawa President) and a fantastic host committee comprised of board members and local volunteers. In total, over 100 individuals and volunteers were involved in hosting the Nationals in back-to-back years: a fantastic accomplishment and two exceptionally well-hosted national events.

Spring 2019. Baseball Oshawa celebrated its 70th Anniversary in 2019 with various special events. Baseball Oshawa paid tribute to three of the greatest teams in the OLMBA 70-year history.

Players from 1984, 1994 and 1999 Ontario Championship teams were honoured on Monday, July 29, at Kinsmen Stadium. As we celebrate our 70th year, we honour these teams on the 35th, 25th and 20th Anniversary of their provincial titles. The players and coaches got together once more as they were presented with team photos and T-shirts to acknowledge their Ontario titles. The 1984 Senior Legionaires Championship team was comprised of Steve Parker, Larry Healey, Bryan Wilson, Doug Stone, Gary Carroll, Bill Hughes, Jim Sarnovsky, Mike Noonan, Scott Cawker (Coach/Player), Doug Pickell, Dave Ashton (Player/Coach), Clare Osbourne, Keith Powell, Bob McMillan, Bryan Rothery. The 1994 Ontario Midget Championship team members were GM Mark Orton, Head coach Rob Snodden, Assistant Coaches: George Patfield, and Ed Portch, Players: Hans Schnell, Jason French, Alan Wilson, Ron Hatch, Nathan Bird, Jamie Loney, Darryl Reid, Ryan Sebris, Chad Connolly, Andrew Petti, Tim Patfield, Mike Morozuk, Craig Macklem, Derek Crossman and Derek Purdue. The 1999 Ontario Junior Legionaries championship team featured GM Jim Lutton, Head Coach Troy May, Assistant Coaches: Tom Jenkins, Neil Osborne, and Bat Boy Jamie May Players: Darryl Reid, JP Vittorio, Al Stephens, Ryan Sebris, Shawn Andrews, Jeff Reeves, Brad Webster, Ryan Mellor, Jared McCord, Lee Delfino, Ryan Colburn, Billy Jones, Mark Webster, Ray Collins, Dustin Jackson, JP Skwarchewsky, Adam Dupont, Mark Cairns, Derek Crossman, Mike Feret, Mick Kurhan and Scott Thompson.

Summer 2019. The Oshawa Junior Legionaires, skippered by Scott Cawker, captured the first-ever National Championship title in Baseball Oshawa OLMBA history. After advancing from the Ontario Junior Elims proudly hosted by Oshawa, the team ran the table in Quebec to win Gold in 2019.

Summer 2020 and 2021. The Baseball Oshawa Executive and Board's dedicated efforts and perseverance led to baseball continuing safely through two summers of the COVID-19 Pandemic. 

In the summer of 2022, Baseball Oshawa was able to obtain three significant grants due to the tireless efforts of our Treasurer, Bryan Howcroft. The COVID-19 Pandemic had a negative impact on the association and left Baseball Oshawa seeking financial assistance.

The association received $15,000 from Canadian Tire, $5000 from the City of Oshawa, and $57,500 from the Ontario Trillium foundation over the last 2 years. These funds allowed us to replace equipment, offer new programs and enhance the excellent experience we offer the kids of Oshawa.

FALL 2022: President Ken Babcock stepped down after 10 full seasons guiding the association. He developed many new initiatives and best practices.  He created Baseball Day in Oshawa at Kinsmen Stadium to bring house league and rep players together for a fun and educational day of baseball. He spearheaded the creation of the Elite teams, which saw the teams start in the Elite League of Baseball of Ontario and then oversaw the transition to the more competitive Premier Baseball League. 

*OLMBA President Troy May passed away on July 19, 2006 from injuries sustained in a motor vehicle accident on Sunday, July 16, 2006. Vice-President of Rep Baseball Dave Sheridan assumed the duties of President as per the OLMBA constitution. As per the constitution Dave remained in control until elections for officers was held at the Annual General Meeting (AGM) in October of 2006.