Every Cheltenham Town season on record, from 1933–34 to 2026–27 — league record, finishing position and leading scorer. Click a season for every match it contained.
| Season | Division | P | W | D | L | GF | GA | Pos | Leading scorer |
|---|---|---|---|---|---|---|---|---|---|
| 1933–34 | 3 | 2 | 0 | 1 | 8 | 5 | 5 | ||
| 1935–36 | 2 | 0 | 1 | 1 | 0 | 6 | 6 | ||
| 1937–38 | 1 | 0 | 0 | 1 | 0 | 3 | 11 | ||
| 1938–39 | 2 | 0 | 1 | 1 | 1 | 2 | 13 | ||
| 1945–46 | 2 | 0 | 0 | 2 | 2 | 5 | 4 | ||
| 1946–47 | 1 | 0 | 0 | 1 | 2 | 4 | 9 | ||
| 1947–48 | 2 | 1 | 0 | 1 | 7 | 4 | 10 | ||
| 1950–51 | 1 | 0 | 0 | 1 | 1 | 3 | 6 | ||
| 1956–57 | 1 | 0 | 0 | 1 | 1 | 2 | 4 | ||
| 1959–60 | 2 | 0 | 1 | 1 | 0 | 3 | 4 | ||
| 1962–63 | 1 | 0 | 0 | 1 | 3 | 6 | 9 | ||
| 1968–69 | 1 | 0 | 0 | 1 | 0 | 4 | 19 | ||
| 1969–70 | 1 | 0 | 0 | 1 | 0 | 2 | 10 | R1 | |
| 1970–71 | 1 | 0 | 0 | 1 | 0 | 4 | 15 | QR3 | |
| 1974–75 | 1 | 0 | 0 | 1 | 1 | 3 | 6 | R2 | |
| 1987–88 | National League | 1 | 0 | 0 | 1 | 1 | 5 | 13 | |
| 1990–91 | National League | 1 | 0 | 0 | 1 | 0 | 1 | 16 | |
| 1992–93 | Southern League | 3 | 1 | 1 | 1 | 3 | 5 | 2 | |
| 1996–97 | Southern League | 2 | 0 | 1 | 1 | 1 | 3 | 2 | Promoted to Conference after Gresley F.C. ground failed Conference requirements |
| 1997–98 | National League | 5 | 2 | 2 | 1 | 7 | 5 | 2 | 1997–98 FA Trophy winners |
| 1998–99 | National League | 1 | 0 | 0 | 1 | 0 | 1 | 1 | Promoted to The Football League for the first time |
| 1999–00 | Third Division | 50 | 21 | 11 | 18 | 55 | 49 | 8 | |
| 2000–01 | Third Division | 50 | 19 | 15 | 16 | 64 | 59 | 9 | |
| 2001–02 | Third Division | 55 | 26 | 17 | 12 | 84 | 58 | 4 | Promoted to Division Two via the play-offs. Highest position achieved in FA Cup |
| 2002–03 | Second Division | 51 | 13 | 18 | 20 | 60 | 80 | 21 | |
| 2003–04 | Third Division | 50 | 16 | 14 | 20 | 65 | 77 | 14 | |
| 2004–05 | League Two | 48 | 16 | 12 | 20 | 53 | 59 | 14 | |
| 2005–06 | League Two | 57 | 25 | 18 | 14 | 80 | 61 | 5 | Promoted to League One via the play-offs |
| 2006–07 | League One | 50 | 16 | 10 | 24 | 52 | 67 | 17 | |
| 2007–08 | League One | 51 | 14 | 14 | 23 | 49 | 73 | 19 | |
| 2008–09 | League One | 53 | 11 | 15 | 27 | 59 | 101 | 23 | Worst goal difference and joint worst win percentage (19.6%) in club history |
| 2009–10 | League Two | 49 | 10 | 18 | 21 | 57 | 79 | 22 | |
| 2010–11 | League Two | 50 | 14 | 13 | 23 | 58 | 84 | 17 | |
| 2011–12 | League Two | 56 | 29 | 8 | 19 | 81 | 66 | 6 | Losing play-off finalists |
| 2012–13 | League Two | 54 | 22 | 17 | 15 | 68 | 65 | 5 | Losing play-off semi-finalists |
| 2013–14 | League Two | 50 | 14 | 17 | 19 | 61 | 72 | 17 | |
| 2014–15 | League Two | 51 | 11 | 14 | 26 | 48 | 73 | 23 | Joint worst win percentage in club history (19.6%). Only 5 clean sheets |
| 2015–16 | National League | 1 | 0 | 0 | 1 | 0 | 1 | 1 | Best Goal Difference in club history |
| 2016–17 | League Two | 56 | 17 | 15 | 24 | 66 | 80 | 21 | |
| 2017–18 | League Two | 49 | 14 | 12 | 23 | 73 | 82 | 17 | |
| 2018–19 | League Two | 56 | 18 | 16 | 22 | 72 | 82 | 16 | |
| 2019–20 | League Two | 45 | 20 | 14 | 11 | 65 | 48 | 4 | End of regular season cancelled due to COVID-19 pandemic. Final standing based on points per game. Losing play-off semi-finalists |
| 2020–21 | League Two | 56 | 31 | 10 | 15 | 75 | 51 | 1 | Promoted as champions. Nearly all games played behind closed doors due to the COVID-19 pandemic |
| 2021–22 | League One | 55 | 15 | 21 | 19 | 77 | 94 | 15 | Highest position achieved in English football system |
| 2022–23 | League One | 55 | 18 | 14 | 23 | 60 | 77 | 16 | |
| 2023–24 | League One | 51 | 12 | 8 | 31 | 43 | 82 | 21 | |
| 2024–25 | League Two | 55 | 22 | 12 | 21 | 75 | 83 | 15 | |
| 2025–26 | League Two | 54 | 17 | 11 | 26 | 64 | 91 | 18 | |
| 2026–27 | 3 | 1 | 0 | 2 | 4 | 6 |