Number five in our countdown is one of the more uncomfortable entries to write, not because the numbers do not stack up, but because they tell a story that Lincoln City supporters remember all too clearly.
Ashley Grimes was prolific, devastatingly so for a time, and yet his spell at Sincil Bank remains inseparable from relegation and collapse.
Grimes scored 15 league goals from just 27 outings for Lincoln City, a return that works out at 0.56 goals per game, a ratio that places him among the most efficient finishers the club has seen in the modern era.
That statistic alone demands his place this high in the list.
Ashley Grimes (0.56 goals per game)
Arriving on loan during the 2010–11 season, Grimes made an immediate impact. After a brief bedding-in period, his goals came in a relentless burst. Across his first four months at the club, he scored 17 times in all competitions, a run of form that quite literally kept Lincoln alive through the winter. Without those goals, relegation would have been confirmed long before spring.
The partnership with Delroy Facey was central to that surge. Facey’s physical presence and ability to occupy defenders allowed Grimes to operate as the diminutive, intelligent forward he was. Sharp movement, quick feet, and an instinctive understanding of space made him lethal inside the box. For a period, it looked as though that pairing could carry City to a respectable mid-table finish.
His goals arrived regularly and often decisively. A debut strike against Morecambe, further goals against Hereford and Bradford, and then an extraordinary January that included five goals in a single month, highlighted by a hat-trick away at Stockport in a 4-3 win. February and March brought more of the same, with braces against Morecambe and Southend as Grimes continued to carry the attacking burden almost single-handedly.
But the season turned, and when it did, everything that had worked began to unravel.
Facey’s injury proved pivotal. Trevor Carson’s departure removed another pillar. Grimes became increasingly isolated at the top of the pitch. As Lincoln retreated deeper and deeper into games, the forward was left chasing lost causes while the ball spent most of its time in our defensive third.
His final goal came in a 2-1 defeat at Stevenage, a moment that felt symbolic even at the time. From that point on, survival stopped feeling possible. Grimes still worked, still showed flashes of his ability, but the confidence had drained from the side. He began to embody both the quality and the fragility of a team that would go down without resistance.
The abuse he received leaving the pitch on the day relegation was confirmed remains one of the more uncomfortable memories of that season. It was unfair, but it spoke to the frustration and helplessness that had consumed the club by that point.
There was genuine interest from both Grimes and Steve Tilson in making the move permanent. On footballing merit alone, it made sense. However, relegation changed the equation. Grimes had already indicated that he did not see his future in the Conference, and Lincoln City’s drop out of the Football League effectively closed the door.
In the years since, his career has drifted, climbing a division and then falling away again. His return to Sincil Bank with Southport ended in controversy rather than nostalgia, sent off for kicking out at Alex Woodyard in the first half, a reminder that time does not always soften memories.
Ashley Grimes’ Lincoln City spell is a strange one to assess emotionally, but statistically it is clear. 15 league goals in 27 games is elite output by any standard. His goals kept us alive far longer than we had any right to be, even if the inevitable could not be avoided.
That efficiency secures his place at number five in this countdown. A prolific striker, a fleeting saviour, and a reminder that even the sharpest finishing cannot always compensate for a side that is quietly falling apart around it.
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