1969
Operation Springboard is conceived by two former offenders. They begin providing counselling services and transportation to family members wishing to visit incarcerated offenders.

1974
Operation Springboard incorporates. The agency now provides transportation to all major Ontario correctional institutions & penitentiaries as well as support services to ex-inmates and their families.

1985
The bus service provides transportation for 1,711 clients, and the total budget is over $174,000.00

The board of directors of the John Howard Society of Metropolitan Toronto assumes responsibility for Operation Springboard, which becomes a separate corporate entity within the John Howard organization.

1987
Operation Springboard separates from the John Howard Society. The organization now offers 10 group homes, a 24-hour distress line for inmates, a community service order program, counselling, education, and job services, and a literacy program. Its total budget exceeds $6 million.

1994
At the twentieth anniversary of its incorporation, Springboard has 14 locations in Ontario providing services to over 8,800 people each year, with an annual budget of over $8.5 million.

1999
Springboard celebrates its thirtieth year since conception. Its programs and services assist 9,400 people in 1998-1999.

2005
Springboard releases a 5-year strategic plan highlighting priorities and goals. With the participation and support of the community, over 20 programs help people in the areas of justice, services for the developmentally disabled, housing, and finding and keeping employment. The agency now reaches up to 13,000 people per year and administers an annual budget of 11 million dollars.