This page lists the head-to-head record of Cittadella vs Grosseto including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | Grosseto | Cittadella | Draws |
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| Total Matches | 12 | 3 | 3 | 6 |
| At Stadio Carlo Zecchini | 6 | 1 | 3 | 2 |
| At Stadio P. Tombolato | 6 | 2 | 0 | 4 |
| Serie B Matches | 10 | 3 | 3 | 4 |
| Serie C1 - A Matches | 2 | 0 | 0 | 2 |
| Total Goals Scored | 31 | 17 | 14 | |
Last 50 Grosseto vs Cittadella Matches
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| 2013 26 January | | Serie B | Grosseto | 3 - 1 | Cittadella |
| 2012 1 September | | Serie B | Cittadella | 2 - 1 | Grosseto |
| 2012 17 March | | Serie B | Grosseto | 2 - 2 | Cittadella |
| 2011 15 October | | Serie B | Cittadella | 2 - 0 | Grosseto |
| 2011 27 March | | Serie B | Grosseto | 1 - 1 | Cittadella |
| 2010 30 October | | Serie B | Cittadella | 2 - 1 | Grosseto |
| 2010 13 February | | Serie B | Grosseto | 3 - 0 | Cittadella |
| 2009 12 September | | Serie B | Cittadella | 1 - 1 | Grosseto |
| 2009 2 May | | Serie B | Cittadella | 0 - 2 | Grosseto |
| 2008 6 December | | Serie B | Grosseto | 1 - 1 | Cittadella |
| 2007 3 March | | Serie C1 - A | Cittadella | 0 - 0 | Grosseto |
| 2006 21 October | | Serie C1 - A | Grosseto | 2 - 2 | Cittadella |
Biggest Grosseto Victory vs Cittadella
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| 2010 13 February | | Serie B | Grosseto | 3 - 0 | Cittadella |
Biggest Cittadella Victory vs Grosseto
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| 2011 15 October | | Serie B | Cittadella | 2 - 0 | Grosseto |
Biggest Grosseto Defeat vs Cittadella
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| 2011 15 October | | Serie B | Cittadella | 2 - 0 | Grosseto |
Biggest Cittadella Defeat vs Grosseto
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| 2010 13 February | | Serie B | Grosseto | 3 - 0 | Cittadella |
Last 5 Grosseto Home Matches
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| 2022 14 April | | Serie C1 - A | Grosseto | 0 - 2 | Lucchese |
| 2022 3 April | | Serie C1 - A | Grosseto | 0 - 0 | Robur Siena |
| 2022 19 March | | Serie C1 - A | Grosseto | 1 - 0 | Virtus Entella |
| 2022 15 March | | Serie C1 - A | Grosseto | 0 - 0 | Pontedera |
| 2022 6 March | | Serie C1 - A | Grosseto | 2 - 0 | Imolese |
Last 5 Cittadella Home Matches
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| 2025 15 November | | Serie C1 - A | Cittadella | 1 - 0 | Arzignano Valchiampo |
| 2025 2 November | | Serie C1 - A | Cittadella | 2 - 1 | Pro Vercelli |
| 2025 12 October | | Serie C1 - A | Cittadella | 1 - 0 | Triestina |
| 2025 29 September | | Serie C1 - A | Cittadella | 0 - 0 | Pro Patria |
| 2025 25 September | | Serie C1 - A | Cittadella | 0 - 1 | Lumezzane |
Last 5 Grosseto Away Matches
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| 2022 23 April | | Serie C1 - A | Olbia | 3 - 1 | Grosseto |
| 2022 9 April | | Serie C1 - A | Pescara | 2 - 1 | Grosseto |
| 2022 27 March | | Serie C1 - A | Montevarchi Calcio | 1 - 1 | Grosseto |
| 2022 12 March | | Serie C1 - A | Vis Pesaro | 2 - 1 | Grosseto |
| 2022 27 February | | Serie C1 - A | Teramo | 2 - 1 | Grosseto |
Last 5 Cittadella Away Matches
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| 2025 23 November | | Serie C1 - A | Lecco | 0 - 1 | Cittadella |
| 2025 8 November | | Serie C1 - A | Dolomiti Bellunesi | 0 - 1 | Cittadella |
| 2025 27 October | | Serie C1 - A | Inter II | 0 - 1 | Cittadella |
| 2025 18 October | | Serie C1 - A | Ospitaletto | 1 - 2 | Cittadella |
| 2025 4 October | | Serie C1 - A | Renate | 0 - 0 | Cittadella |