[6][8] Bennett joined Second Division club Small Heath in 1896, and made his debut on 26 September away to Burton Swifts, playing at outside right after Bill Edwards was dropped and Jimmy Inglis moved to outside left.
The match ended as a 1–1 draw and the Birmingham Daily Gazette described Bennett as "a smart and clever youth, who shoots and centres in capital style, and [whose] debut in the first eleven was decidedly promising.
[13] Playing at inside right, he scored twice in a 3–0 win against Luton Town, set up the third goal for Tom Scrivens with an "accurately-placed centre",[14] and he and Jack Leonard were reported to have done "surprisingly well on the right wing".
After ten minutes, Bennett gave his team the lead with "a long shot from the wing, [that] passed just under the bar without giving Wilkes a chance.
"[17] They held on to the lead, beat Burnley in the next round, and lost to reigning Football League champions and local rivals Aston Villa in the quarter-final only after a replay.
[18][19] He was able to play in the opening fixture, a goalless draw at home to Liverpool, but a kick on the same leg during the game resulted in an ulcer forming on the shin.
[1] However, Bennett re-signed for Small Heath in March 1903 with a view to making a comeback, and was expected to play for the reserves against Brierley Hill Alliance in the Birmingham League.