With the league being restructured at the end of the 1957/58 season, it would be crucial for the Town to finish in the top half of the table – to avoid having to become founder members of the newly created Fourth Division.
With little money available for transfers, Head set up a youth system, which aimed to develop young players in some of the local leagues.
When the Possibles won the game convincingly, it persuaded Head to start the season with a young team, which included the youngest ever full-back pairing of John Trollope and Terry Wollen – both of whom were aged just seventeen.
This system produced many future Swindon greats – Trollope, Mike Summerbee, Bobby Woodruff, Ernie Hunt, Keith Morgan, Roger Smart, Rod Thomas, David 'Bronco' Layne and Don Rogers to name but a few – and, as they gradually climbed the league table, the team earned the nickname, "Bert's Babes".
As the season went on, more players succumbed to injury – and crucially, the highly rated forward Ernie Hunt was missed most often – firstly with appendicitis, then with a broken foot.
Amazingly, the League allowed the Pompey game to kick off later in the evening, and when Town lost 2–1 at The Dell, Portsmouth knew they needed only a draw to keep them up.
They had been unlucky – but the Town board showed no mercy, rather harshly sacking Head in August 1965 – the man who had previously turned the fortunes of the club.
His wife Ginny had died eight years previously, but he left two sons, David, who played professionally for Reading, and Roger and a daughter, Sue.