| 1954 | Under the direction of Roy Titheridge, the first Douglas Villa Junior team was formed. The players involved in the team gave Douglas Villa AFC its club name. The unique name came from a combination of the name of the inaugural home ground, Douglas Park, and the fact that a number of the founding players lived on the local Villa Street. It's worth noting that Douglas Park, on Cole Street, Masterton West continues to be used by the club as a home ground for our junior sides. |
| 1958 | In 1958 the Senior Club was formed and in 1959, the Douglas Villa Senior team won the Senior Championship. |
| 1969 | In 1969, Douglas Villa completed a hat trick having won the Senior Championship in the 1967, 1968 and 1969 years consecutively. |
| 1970 | Following the clubs' success, Douglas Villa entered into the Western League - the feeder into the Central League, winning this the following year and capitalising on our success by also winning the play-off and entry into the Central League at the end of the 1971 season. |
| 1972 | We placed third in the Central League Division 2 in 1972 and were relegated the following year. |
| 1975 | In 1975, we placed second in the Wairarapa League and qualified for the Third Division of the Central League. During our tenure in the Central League which spanned a decade, we finally achieved success at winning the Third Division in 1985 with our seconds team gaining promotion into the Tasman League. |
| 1975 to 2009 | Being researched now! |
| 2009 | We were the local league champions in 2009 and gained promotion into Capital 3 where we played two seasons before being promoted into Capital 2 in 201. We remained here until 2015 where we were relegated to Capital 3 and withdrew from the Capital Division for the 2016 season. |
| 2019 | Completed yet another Hat Trick winning the Local Knockout Cup in 2017, 2018 and 2019 with our Magpies team winning Div 1 undefeated for a consecutive three seasons. In 2019, our top team gained promotion into Capital 4. |
| 2020 | Gas Pro our top team finished second in the season and gained promotion into Cap 3 for the 2021 season. |
| 2021 | In Cap 3 our top team, who re-took the "Magpies" name, finished 2nd on goal difference gaining promotion to Cap 2 for 2022. |
| 2022 | After overcoming an awful start and a coaching change, our DV Senior Men's team finish a creditable 5th in Cap 2. |
| 2023 | Our men's 1st team TUMU Douglas Villa under coach Mark Taylor and Assistant Coach/Manager Riki Riddell finished 2nd to be promoted to Cap 1. Also, DV Cam's Flooring won KO shield and DV Skulls won the KO cup. To cap this all off, we also won club of the year for the 1st time
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| 2024 |
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