In his second year as a trainee he made the first team squad, being an unused substitute in the 2–2 home Football League draw with Scarborough on 15 October 1988 before playing a full ninety minutes in the 3–1 home victory over Enfield four days later which secured the Imps the James Thompson Championship Shield, an annual contest between the winners of the Football Conference and FA Trophy.
His performances for Guisborough Town attracted attention and, on 14 March 1994, John Beck paid £10,000 to secure his services for Preston North End.
On 31 March 1994 he joined Bromsgrove Rovers on loan[3] for a month, debuting in the 1-0 Football Conference home defeat to Slough Town on 2 April 1994.
The injury kept him out of action for ten months but he returned in spectacular style, scoring less than a minute into his comeback at the Imps defeated Carlisle United 5–0 at Sincil Bank on 4 March 2000.
[9] However, the injury became infected, causing Holmes to spend five days in hospital over the New Year period[10] and after remaining in pain, he learnt the knee required an operation which would keep him out for the remainder of the season[11] and he underwent surgery on 14 February 2002.