4 – Harry Toffolo
I’m going to get pelters for Toff not being higher, aren’t I?
Millwall released him without him playing a first-team game, allowing us to bring him in on a free transfer in June 2018. He played all 46 league matches as we won the League Two title and earned a place in the PFA Team of the Year, before following Danny and Nicky Cowley to Huddersfield Town for an undisclosed fee in January 2020. After reaching the Championship play-off final with Town, he moved to Nottingham Forest in 2022 and played Premier League football, then joined Charlotte FC following his Forest departure in 2025.
He was an example of the model before we really had the model, arriving at a time when developing players for a substantial resale profit wasn’t quite so central to the conversation. He was excellent in the League Two title-winning side, adapted to the step up and, by the time he left in January 2020, had given us both a significant contribution on the pitch and a financial return on a free transfer.
His subsequent progress into top-flight football only reinforces the quality of that initial recruitment decision. Some will think fourth is too low, and I can understand that, because there is very little missing from his case: ability, impact, profit and a career that continued to move upwards after Lincoln. For me, he was a superb signing, even if four others ultimately edge ahead of him
Hard to argue with the list … totally agree with comments about Harry Anderson !