The 1959 Italian Grand Prix was held at Monza on 13th September 1959 and was penultimate race of that year’s World Drivers Championship. The 29th Italian Grand Prix, and the 24th to be held at Monza, was run over 72 laps of the five kilometre circuit, for a total race distance of 414 kilometres.

The race was a strategic one, won by conserving tyres, Jack Brabham having identified that front tyre wear on the Monza circuit was a real concern. To off-set this, Brabham fitted harder wearing Dunlop sports car tyres to his left front wheel to add durability over the course of the race. 

As Stirling, having noted Brabham’s tyre choice, recalled “thanks to some quick thinking and good contacts, we did the same”. His mechanic, Alf Francis, fitted the same tyres to Stirling’s rear engine Cooper-Climax. To add to the subterfuge, they switched the front wheels from bolts to knock-off centre fixings, both as an insurance policy and to lull Ferrari into thinking they would stop.

Stirling set a record 1 minute 39.7 second lap during qualifying, putting him on pole, with Tony Brooks, the only other driver under the 1 minute 40 mark in his #30 Ferrari 246, in second , followed by Jack Brabham, in the second Cooper-Climax, in third place on the grid. 

At the start of the race, a cloud of smoke came from the back of Brooks' Ferrari, signalling a broken piston and the end of his race, as the Coopers on each side of him shot ahead. Stirling lead Phil Hill, in the #32 Ferrari 246, on lap one, from Brabham in the #12 Cooper and Dan Gurney in the #36 Ferrari.

On lap two Stirling let Hill take the lead and was content to sit behind and let the Ferrari set the pace, conserving his tyres by taking the corners gently and catching the Ferrari up again on acceleration.

From laps 10 to 20 the scene at the head of the race remained unchanged, the distance covering the three cars being the same all the time.

The two American Ferrari drivers could do nothing about getting rid of Stirling’s Cooper, who recalled that “it was crucially important to conserve my tyres in the early stages of the race”. Stirling was content to run his race at the speed of Hill's Ferrari and no more, banking on the fact that the both Ferraris’ would wear their tyres out faster than his.

The outcome of the race was decided between laps 33 and 36, when all three leading Ferraris’, including Cliff Allison’s, car running in 4th place, pitted for tyres.

Within the space of three laps the Ferrari team had removed all the pressure from Stirling, leaving him out on his own in the lead by some 60 seconds. Ferrari had assumed that Stirling would have to stop to change tyres, however as he had been conserving them during the opening phase of the race, by letting Hill set the pace, he could now ease off by a small amount, which made all the difference to the tyre wear.

The race order following the pit stops was now Stirling, Hill, Brabham, Gurney, Allison, all on the same lap. Stirling tyres held and he eased home, winning the 1959 Italian Grand Prix by 46.7 seconds from Hill, with Brabham picking up four crucial championship points, by taking third place.

Brabham left Monza with a 5.5 point lead over Stirling in the World Drivers Championship, with Brooks a further 2.5 points behind.  As Stirling recalled “it would be a long wait” before the Championship deciding United States Grand Prix, which took place three months later in December at Sebring.

Sadly for Stirling, his 1959 Championship bid was halted on lap 5 of the US Grand Prix by a broken gear box.