Glenn had begun his career as a trainee with Crystal Palace, but failed to break into their first team. He was released in the summer of 2006 and the 21 year old right back became one of Diamonds new manager Paul Hart's first signings, replacing the departed Rob Gier. His versatility allowed him to also play in a midfield role. During the later half of the season however, he went out on a one month loan to rivals Kidderminster Harriers on 21 March 2007 before returning.

He was transfer listed by manager Garry Hill in May and joined Crawley Town on 10 July 2007. After more than four years at the Broadfield Stadium which included promotion to the Football League, Glenn went out on a three month loan deal to Conference side Fleetwood Town on 12 October 2011, but was recalled in December after 5 appearances.

Appearances

2006/2007 - squad number 2

Conf	12.8.06	Crawley Town (A)
Conf	15.8.06	Grays Athletic (H)
Conf	19.8.06	Forest Green (H)
Conf	26.8.06	Southport (A)
Conf	28.8.06	York City (H)
Conf	1.9.06	Kidderminster (A)
Conf	9.9.06	Altrincham (H)
Conf	12.9.06	Tamworth (A)
Conf	16.9.06	Stafford Rgrs (A)
Conf	19.9.06	Gravesend&Nflt(H)
Conf	23.9.06	Woking (A)
Conf	30.9.06	Burton Albion (H)
Conf	3.10.06	Morecambe (A)
Conf	6.10.06	Stevenage Boro(H)	as sub
Conf	10.10.06	Halifax Town (H)	as sub
Conf	14.10.06	Northwich Vic (A)
Conf	21.10.06	Weymouth (A)
FAC4q	28.10.06	Altrincham (H)
Conf	4.11.06	Dagenham&Red(H)
FAC1	11.11.06	Yeovil Town (H)
Conf	25.11.06	Aldershot Tn (H)
FAC2	2.12.06	Tamworth (H)
Conf	26.12.06	Cambridge Utd (A)
Conf	30.12.06	Gravesend&Nflt(A)
Conf	6.1.07	Altrincham (A)
FAT2	13.1.07	Witton Albion (A)
Conf	20.1.07	Stafford Rgrs (H)
Conf	23.1.07	Cambridge Utd (H)
Conf	29.1.07	Oxford Utd (A)
FAT3	3.2.07	Gravesend&Nflt(A)
HSCSF	6.2.07	Rothwell Town (H)
Conf	10.2.07	Dagenham&Rdg(A)
Conf	17.2.07	St.Albans (H)
Conf	24.2.07	Aldershot Town(A)	as sub
HSCF	20.3.07	Woodford Utd (A)
Conf	21.4.07	Woking (H)
Conf	23.4.07	Northwich Vic (H)
Conf	28.4.07	Burton Albion (A)	as sub