During their following 1968-69 Fourth Division campaign, Ashman gave a professional debut to future England captain and manager Kevin Keegan. All of Keegan's 141 appearances for the club came under Ashman's management and as recently as 2018 he hailed that Ashman was "a man who deserved a great deal of respect." Ashman personally drove Keegan to Anfield after negotiating a £33,000 sale for him, having famously asked the midfielder: "Have you got a good suit? Well, you’re going to need one. Where you’re heading, you’re going to need to look smart."