I used to get a cheap Juventus shirt every summer on holiday in the mid 90s, so it started with the likes of Baggio and Ravanelli leaving. I turned my hand to Blades players getting Deane 10 on my home shirt and Fjortoft 9 on my away shirt at the start of 97-98.
The worst choice I made was Smith 19. I didn't even like the shirt, it's not a very interesting name, he wasn't that good (just scored a few goals early that season) and then buggered off to Huddersfield. I think after that I just stuck with my own name and my favourite #15.
Edit - remembered some others, notably Kabba who was barely ever fit after I got his name on my shirt. I spent a long time weighing up the embarrassment of having Thirlwell on my shirt versus getting rid of him.