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The 2008–09 Maltese First Division Knock-Out was a knockout tournament for Maltese football clubs playing in the First Division. This year's format differs from the previous 2 years in that the simple knock-out has been replaced by two groups, the top two from each qualifying for the semi-finals. The competition started on 13 September 2008 and finished on 10 May 2009, with the final. The final was contested between the First Division champions Dingli Swallows and St. Patrick. St. Patrick won 2-0.
| Pos | Team | Pld | W | D | L | GF | GA | GD | Pts | Qualification | DIN | PIE | MQA | RAB | VIT | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Dingli Swallows | 4 | 3 | 1 | 0 | 5 | 1 | +4 | 10 | Advance to knockout phase | — | 0–0 | 2–1 | 2–0 | 1–0 | |
| 2 | Pietà Hotspurs | 4 | 2 | 2 | 0 | 4 | 1 | +3 | 8 | — | 1–0 | 0–0 | 3–1 | |||
| 3 | Mqabba | 4 | 2 | 0 | 2 | 7 | 6 | +1 | 6 | — | 3–1 | 3–2 | ||||
| 4 | Rabat Ajax | 4 | 0 | 2 | 2 | 2 | 6 | −4 | 2 | — | 1–1 | |||||
| 5 | Vittoriosa Stars | 4 | 0 | 1 | 3 | 4 | 8 | −4 | 1 | — |
| Pos | Team | Pld | W | D | L | GF | GA | GD | Pts | Qualification | STP | MOS | STG | SEN | SĠW | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | St. Patrick | 4 | 3 | 0 | 1 | 12 | 2 | +10 | 9 | Advance to knockout phase | — | 0–1 | 4–0 | 4–0 | 4–1 | |
| 2 | Mosta | 4 | 2 | 2 | 0 | 5 | 3 | +2 | 8 | — | 1–1 | 1–1 | 2–1 | |||
| 3 | St. George's | 4 | 1 | 2 | 1 | 4 | 6 | −2 | 5 | — | 2–0 | 1–1 | ||||
| 4 | Senglea Athletic | 4 | 1 | 1 | 2 | 3 | 8 | −5 | 4 | — | 2–1 | |||||
| 5 | San Ġwann | 4 | 0 | 1 | 3 | 4 | 9 | −5 | 1 | — |
| Team 1 | Score | Team 2 |
|---|---|---|
| 23 May 2009 | ||
| Dingli Swallows | 5–1 | Mosta |
| Pieta Hotspurs | 1–3 (a.e.t.) | St. Patrick |
| Team 1 | Score | Team 2 |
|---|---|---|
| 31 May 2009 | ||
| Dingli Swallows | 0–2 | St. Patrick |
