| Current: | 2018–19 Gibraltar Division 2 Cup |
| Number Of Teams: | 7 teams from Second Division |
| Region: |  Gibraltar |
| Current Champions: | Bruno's Magpies (2018–19) |
| Most Successful Club: | Europa Point PwC Laguna (2 titles) |
The Gibraltar Division 2 Cup is a special football tournament exclusively organized for clubs participating in the Second Division.[1]
On 2 March 2017 the Gibraltar Football Association announced the signing of a sponsorship agreement with Chestertons Gibraltar, due to which the competition was renamed "The Chestertons Cup".[2] Chestertons Gibraltar became the first sponsor of the competition since its inception. No tournament as held in 2018 due to redevelopments at Victoria Stadium, but the competition returned in the 2018–19 season.
| Club | Manager | Captain | Kit supplier | Sponsor | 2017–18 |
|---|---|---|---|---|---|
| Bruno's Magpies | David Wilson | Ross Gray | Nike | GVC Holdings Chestertons | 3rd |
| College 1975 | Nolan Bosio | Nazim Hughes | Joma | 7th | |
| Europa Point | Stefan Oliva | Luanvi | Sunborn Yacht Hotels | 4th | |
| Hound Dogs | Chris Gomez | Ivan Borg | Joma | 8th | |
| Leo FC |  Francisco Sanchez |  Clément Loubière | Errea | 5th | |
| Manchester 62 | Jonathan Sodi |  Christian Toncheff | Joma | CEPSA GIB | |
| Olympique 13 | Ángel Parla-Díaz | Andrew Lopez | Uhlsport | Hungry Monkey | 2nd |
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| Club | Titles | Years | |
|---|---|---|---|
| Europa Point | 2 | 2015, 2016 | |
| PwC Laguna | 2 | 2006, 2008 | |
| Glacis United Res. | 2 | 2005, 2007 | |
| Bruno's Magpies | 1 | 2018–19 | |
| Gibraltar Phoenix | 1 | 2017 | |
| Lions Pilots | 1 | 2014 | |
| Lynx | 1 | 2012 | |
| Rock Cosmos | 1 | 2011 | |
| Europa | 1 | 2010 |