Kingsway's extensive authority and services have been combined through a number of acquisitions extending over a period of more than four decades. Some of the major events in Kingsway's history include:
| 1941 | Beauchamp Express was purchased, giving operating authority between Toronto and Hamilton with all intermediate points. | |
| 1943 | St. Michel Express was purchased, providing service into Valleyfield, P.Q. | |
| 1951 | Pelland Transport was purchased, providing service into Sorel, P.Q. | |
| 1952 | Raitar Transport Ltd. of Waterloo was purchased. This acquisition provided routes to Hamilton, Windsor and Niagara Falls. Kingsway was the first carrier to be able to offer direct service from Windsor to Quebec City. | |
| 1953 | Colossal Lines Limited acquired and extended service into New York City and New Jersey. | |
| 1955 | Purchase of Maroon Cartage gives operating authority into the Detroit/St. Mary's River area, thus providing service to Metropolitan Detroit. | |
| 1957 | Gosset and Sons Transport Limited of Calgary purchased with abilities to serve all of Alberta to and from Eastern Canada. | |
| Rights to operate into Buffalo were obtained with the purchase of Kuhn Cartage. | ||
| Arrow Transit Line of Toronto obtained, along with their authorities to serve all major Southern Ontario cities and off-line destinations to Manitoba. | ||
| 1958 | New Winnipeg Terminal opened February 28th, 1958. | |
| 1959 | Granby Terminal built. | |
| 1960 | Drummond Transit Lines added, giving access to Drummondville and St. Hyacinthe. | |
| 1961 | Dalewood Transports Limited and Rice and Trimble acquired. Dalewood allowed Kingsway to serve North Bay, Sudbury, Sault Ste. Marie, Thunder Bay and points to the West. Included in the Dalewood purchase was acquisition of Secord Transport and T.W. Sayle. | |
| Rice and Trimble's acquisition allowed Kingsway to serve the Metropolitan Vancouver area to Alberta, Saskatchewan and Manitoba. | ||
| 1962 | Gosset, Arrow, Rice and Trimble were merged to form Kingsway Freightlines Limited. | |
| 1965 | The acquisition of John Kron and Sons Limited was completed and Kingsway was able to service Winnipeg through to the Lakehead as well as Red Lake, Dryden, Fort Frances, Kenora and Sioux Lookout. | |
| The purchase of Gaucher Transport Inc. gave Kingsway rights between Asbestos, P.Q. and Sherbrooke. | ||
| 1968 | Northern Transports Ltd. was purchased and gave Kingsway rights in Ontario to service points such as Collingwood, Orangeville, Owen Sound, Stayner and points in the Bruce Peninsula. | |
| The corporate organization was restructured and the administration office was located in Rexdale. Operating authority and responsibility was entrusted to the 4 division managers. | ||
| 1970 | Laurentide Transports Ltd. was obtained, allowing Kingsway to serve St. Therese, St Jerome, Ste. Scholastique and the Laurentians. | |
| 1972 | Servall Transports Limited was established to serve the truckload market in Ontario. | |
| Acquisition of Nu-Way Express Ltd. of Yorkton, Saskatchewan was completed and Kingsway developed operations in each of the provinces from Quebec to British Columbia. Terminals in Regina and Saskatoon were added with this purchase. | ||
| New Ottawa terminal opened. | ||
| 1974 | Operating authority was received to cross the international boundary at Fort Frances, Ontario and International Falls, Minnesota. | |
| C.O.B.I.S. (Computer On-line Billing Information System) was implemented, a first for the Canadian trucking industry. | ||
| Montreal and Sudbury terminals expanded. New terminals at Windsor, North Bay and Vancouver. | ||
| Licenses from Cayer Transport were purchased, providing routes between Quebec City, St. Raymond and Montreal. | ||
| 1975 | Major renovations to Montreal terminal completed. | |
| 1976 | Expansion of the Thunder Bay terminal and the addition of new facilities at Detroit, Sault Ste. Marie, and Edmonton. | |
| Kourier, a small package carrier, was developed with initial service between Ontario and Quebec. | ||
| 1977 | John N. Brocklesby Transport Ltd., heavy hauling and machinery moving operation, was added as one of Kingsway's divisions. | |
| 1978 | New terminals facilities at Winnipeg and Saskatoon. | |
| 1979 | The authorities of Queensway Transports Inc. were acquired, providing a direct route from the New York City area to Buffalo. Authority to service Rochester and Watkins Glen were also included. This firm's name has been changed to Kingsway Inc. | |
| Servall extends their services to the West. | ||
| Kourier extends their services into Western Canada. | ||
| 1980 | Yukon Freight Lines Limited was acquired, giving Kingsway access to Ft. McMurray, Whitehorse, the Yukon and Northwest Territories. | |
| New terminals in London, Buffalo, Grande Prairie and Three Rivers opened. | ||
| 1981 | Kingsway Inc. operating authority extended to Syracuse, N.Y. Terminal opened June, 1981. | |
| By 1981 Kingsway Transports Ltd. had become one of the largest regulated common carriers in Canada, specializing in LTL freight. The Company presently has over 1,900 units operating over 45,000 miles on over 1,800 possible routes. Freight is being handled by 47 Company terminals extending from Quebec City and New York to Vancouver. | ||
| 1984 | A management agreement was reached with Star Transfer Limited enabling Kingsway to offer a direct service to Timmins, Kirkland Lake, Kapuskasing, New Liskeard, Cochrane, Iroquois Falls and Hearst. | |
| 1986 | Consolidated Fastfrate purchased from Canadian Steamship Lines shares and assets of Kingsway Transports Limited and other subsidiary companies. Fastfrate better know as a Freight Forwarding Company, was founded September 20,1966. The results of this purchase enabled Consolidated Fastfrate to be a truly North American transportation organization providing various modes to transport to the shipping and receiving public. | |
| 1988 | The Kingsway Group of Companies was purchased and became part of the Federal Industries Transport Group which includes Motorways Canada. Kingsway/Motorways, including agents, have more than 100 terminals to service directly Central, Eastern and Western Canada, along with the Northeastern seaboard of the United States. | |
| 1989 | Kingsway and Motorways were merged in all locations where there was a duplication. Giving a stream line operation that has Kingsway Transports servicing all areas East of Thunder Bay and Motorways servicing all areas West of and including Thunder Bay. | |
| 1992 | The Cabano Group purchased operating rights of Kingsway Transports Limited and Kingsway Transport Inc. Authorities for Quebec, Ontario and U.S.A. east of Chicago. |