During the early 1930s, Winchester management was disappointed with the slow sales of the Model 56 and Model 57.
Potential buyers considered the Model 56 and 57's 22 in (560 mm) barrels too short and the rifles' prices too high.
 The Model 69 was conceived as a lower-priced replacement with a longer 25 in (640 mm) barrel.
The rifle was designed in 1934 by Winchester employee Frank F. Burton, production was announced with the release of Winchester's new price list on 1 January 1935, and the first completed rifles were shipped in March of the same year.

The striker of the Model 69 was cocked by the closing motion of the bolt, and the safety was actuated by grasping the cocking piece at the rear of the bolt, drawing it back, and rotating it, an arrangement similar to the Mosin–Nagant.
The Model 69 used the same standard 5-round box magazine as the Models 52, 56, 57 and 75, allowing optional 10-round magazines and single-shot adapters to be shared.
The magazine was released by depressing a spring-loaded button on the left-hand side of the stock, which was made of plain uncheckered walnut and had a pronounced pistol grip.
The rifle was a takedown design; the barreled action was easily removed by turning a screw under the stock using a penny.
A removable sheetmetal hood for the front sight was available.
Rear sight choices included a barrel-mounted buckhorn sight that was drift-adjustable for windage and a more sophisticated receiver-mounted peep sight.
A composition buttplate was used on all models.

In August 1935, the bolt was redesigned to incorporate a rebounding firing pin in compliance with Canadian import regulations.
In October 1937, the stock was enlarged so the takedown screw would fit flush with the bottom, the forearm was changed to a semi-beavertail shape, and the pistol grip was made more pronounced.

Winchester-branded telescopic sights were first offered in 1937.
Options were a 2¾-power scope with crosshairs or a vertical aiming post and a 5-power scope with crosshairs.
Open sights were retained; the scopes were boxed separately and attached to integral bases on the barrel by the rifle's buyer.
During the early 1930s, Winchester management was disappointed with the slow sales of the Model 56 and Model 57. Potential buyers considered the Model 56 and 57's 22 in (560 mm) barrels too short and the rifles' prices too high.  The Model 69 was conceived as a lower-priced replacement with a longer 25 in (640 mm) barrel. The rifle was designed in 1934 by Winchester employee Frank F. Burton, production was announced with the release of Winchester's new price list on 1 January 1935, and the first completed rifles were shipped in March of the same year.
The striker of the Model 69 was cocked by the closing motion of the bolt, and the safety was actuated by grasping the cocking piece at the rear of the bolt, drawing it back, and rotating it, an arrangement similar to the Mosin–Nagant. The Model 69 used the same standard 5-round box magazine as the Models 52, 56, 57 and 75, allowing optional 10-round magazines and single-shot adapters to be shared. The magazine was released by depressing a spring-loaded button on the left-hand side of the stock, which was made of plain uncheckered walnut and had a pronounced pistol grip. The rifle was a takedown design; the barreled action was easily removed by turning a screw under the stock using a penny. A removable sheetmetal hood for the front sight was available. Rear sight choices included a barrel-mounted buckhorn sight that was drift-adjustable for windage and a more sophisticated receiver-mounted peep sight. A composition buttplate was used on all models.
In August 1935, the bolt was redesigned to incorporate a rebounding firing pin in compliance with Canadian import regulations. In October 1937, the stock was enlarged so the takedown screw would fit flush with the bottom, the forearm was changed to a semi-beavertail shape, and the pistol grip was made more pronounced.
Winchester-branded telescopic sights were first offered in 1937. Options were a 2¾-power scope with crosshairs or a vertical aiming post and a 5-power scope with crosshairs. Open sights were retained; the scopes were boxed separately and attached to integral bases on the barrel by the rifle's buyer.
Winchester Model 69