The second‐generation Cockshutts arrived in 1958. The previous streamlined shapes were replaced by straight lines and a Harvest Gold paint scheme. A three‐point hitch was standard, the electrical system was 12 volts, the brakes were dry disc units, and power steering was offered as an option.

The 540 replaced the 20. It was powered by a 2.4-liter Continental gasoline engine. The 6+2-speed transmission was now the same as that used on the larger models. The 550 came with a 3.2-liter Hercules engine, available in either gasoline or diesel. The 560 initially carried a 4.4-liter Perkins L4, which was replaced the following year by the direct‐injection 4-270. At the top of the range sat the six‐cylinder Hercules model, now numbered 570. For 1961 the engine grew from 4.9 liters to 5.6 liters, and the model was renamed the 570 Super.

In 1962 White purchased Cockshutt, and from then on tractors built by Oliver were sold under the Canadian brand name.

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