The 1928–29 season was Port Vale's tenth consecutive season of football (23rd overall) in the Football League. For the first time in their history they suffered relegation. This was down to poor away form, at home they went a club record 19 games without a draw, picking up all but five of their points in front of their home fans. The season also saw the departure of club legends Tom Page and Wilf Kirkham.

The pre-season saw only the addition of one major player – goalkeeper Jack Prince from Oldham Athletic. Otherwise the club felt confident that they had a nice blend of youth and experience.

The season started with a 4–1 home defeat to Wolves, yet two days later the Vale travelled to The Dell, where they beat Southampton with two Stewart Littlewood goals – this would prove to be their only away victory of the season. Picking up just two wins in September (a 5–2 win over Millwall thanks to a Littlewood hat-trick, and a 2–1 win over Tottenham Hotspur), the club soon found themselves struggling. They also lost 2–1 at Stoke's Victoria Ground in front of 35,288 supporters. Heading into December they won six successive home games to take them into mid-table, including a four-goal haul from Jack Simms to see off Nottingham Forest. December would prove to be the month that killed the Vale. Oakes had a cartilage operation, Gillespie tore an elbow joint, and the team lost six of their seven festive games. In January the popular high-scoring Littlewood was traded to Oldham Athletic for veteran striker Albert Pynegar and £1,300. Falling down the table fast, in late February they were slaughtered 7–1 at Preston North End's Deepdale. Back at The Old Recreation Ground they managed to regularly pick up victories, most notably demolishing West Bromwich Albion 8–1 on 9 March – the biggest victory in the division that season, Pynegar scoring a hat-trick. Further good work picking up three points from Oldham Athletic and beating Chelsea was undone by a horrifying 6–0 defeat at fellow strugglers Barnsley. The "Valiants" beat Bristol City 5–0 in front of a miserable home turnout thanks to a four-goal effort from Pynegar, yet it was too little too late as the club were relegated.

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