United Debut: v. St Johnstone (H) 5/9/59.
Signed From: Alloa Athletic £3,000 27/8/59.
Transferred to: Brechin City 1971.
Jerry Kerr returned to his old club, Aloa Athletic, to secure the services of Gillespie, and in his first season at the club United were promoted to the 1st Division. In Gillespie's time at the club, United went from strength to strength, going from a struggling 2nd Division outfit to European contrenders within 7 years. Gillespie played in all 4 of United's matches in their first ever European games in 1966. A fantastic servent to the club, Gillespie played in just about every position for United, except goalkeeper, and was only booked once in his time at Tannadice. Gillespie played for the Scottish League against the League of Ireland in 1961at Dalymont Park in Dublin, making him the first United player to be honoured by Scotland at any level.
Promotion from 2nd Division 1960
34 Appearances 18 Goals
Inter Cities' Fairs Cup 1966
4 Appearances
| League | Scot Cup | League Cup | Europe | Total | ||||||
| App. | Gls. | App. | Gls. | App. | Gls. | App. | Gls. | App. | Gls. | |
| 1959-60 | 34 | 18 | 2 | 1 | - | - | 1 | - | 37 | 19 |
| 1960-61 | 31 | 14 | 1 | - | 6 | 1 | - | - | 38 | 15 |
| 1961-62 | 32 | 12 | 1 | - | 6 | 3 | - | - | 39 | 15 |
| 1962-63 | 32 | 14 | ? | ? | 4 | 3 | - | - | 36 | 17 |
| 1963-64 | 33 | 10 | 2 | - | 5 | 1 | - | - | 38 | 11 |
| 1964-65 | 31 | 7 | 2 | - | 9 | 4 | - | - | 42 | 13 |
| 1965-66 | 27 | 6 | 3 | - | 6 | 2 | - | - | 36 | 8 |
| 1966-67 | 29 | 6 | 4 | - | 1 | - | 4 | - | 38 | 6 |
| 1967-68 | 30 | 3 | 2 | - | 6 | 1 | - | - | 38 | 4 |
| 1968-69 | 28 | - | 1 | - | 6 | 1 | - | - | 35 | 1 |
| 1969-70 | 34 | 2 | 2 | - | 6 | - | 2 | - | 44 | 2 |
| 1970-71 | 6 | 1 | - | - | 1 | - | 2 | - | 9 | 1 |
|
Total
|
347 | 93 | 28 | 5 | 55 | 13 | 8 | 0 | 438 | 111 |
