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| Day | Date | Time | Competition | Home | Away | Official(s) |
| Tue | 14-May-2024 | 18:45 | Fife Football Development League - U15 | Fair City Whites U15 (FFDL) | Glenrothes Athletic FC 2009's | Ref: Craig Harvey |
| Tue | 14-May-2024 | 19:30 | Friendly Match (Ref only) | Montrose FC U18 | Boys & Girls Club Scotland (Boys U17) | Ref: George Anderson |
| Tue | 14-May-2024 | 19:45 | Scottish Women's Premier League 1 | Montrose Women's FC | Spartans WFC | AR1: Lee Paterson AR2: Kieran Sharp |
| Wed | 15-May-2024 | 19:00 | SWF - C Weir U14 League | Arbroath Youth FC U14 Girls (Yellows) | Jeanfield Swifts Girls U14 (Jets) | Ref: Cameron Chalmers |
| Wed | 15-May-2024 | 18:45 | SWF - East Girls League | Blairgowrie Girls U14 (Bears) | To be Confirmed (F) | Ref: Joshua McCallum |
| Wed | 15-May-2024 | 19:00 | ERSJFA - Midlands League | Carnoustie Panmure JFC | Forfar United JFC | Ref: Duncan Mclullich AR1: Neil Brand AR2: Scott Fullerton |
| Wed | 15-May-2024 | 19:00 | ERSJFA - Midlands League | Dundee St. James JFC | Tayport JFC | Ref: George Anderson |
| Wed | 15-May-2024 | 19:00 | CAS Elite U16 match (£57) | Dundee United FC U16 | Aberdeen FC U16 | Ref: Ruaraidh Garnes |
| Wed | 15-May-2024 | 19:00 | ERSJFA - Midlands League | Dundee Violet JFC | Dundee East Craigie JFC | Ref: Willie Ferguson |
| Wed | 15-May-2024 | 18:15 | SWF - L Clelland U14 League | Dundee West FC Girls U14 (Royals) | Arbroath Youth FC U14 Girls | Ref: Shaunlee Ogilvie |
| Wed | 15-May-2024 | 18:30 | SWF - L Clelland U14 League | Fair City Girls U14’s FC | Bayside Community Football Club U14 Girls | Ref: Craig Harvey |
| Wed | 15-May-2024 | 19:00 | Fife Football Development League - U14 | Fair City Youth FC U14 (FFDL) | Thornton Hibs FC | Ref: Ivan Nsimbi |
| Wed | 15-May-2024 | 19:00 | ERSJFA - Midlands League | Forfar West End JFC | Dundee Downfield JFC | Ref: Lee Paterson |
| Wed | 15-May-2024 | 18:30 | PKYFA - League Match | Jeanfield Swifts 2011's | Scone Thistle Development Blacks 2010s | Ref: Hugh Edens |
| Wed | 15-May-2024 | 18:30 | PKYFA - League Match | Letham Sky Blues 2011's | Breadalbane and Strathtay Youth FC 2011s | Ref: John Thornhill |
| Wed | 15-May-2024 | 19:00 | ERSJFA - Midlands League | Scone Thistle JFC | Coupar Angus JFC | Ref: Jamie McCunnie |
| Thu | 16-May-2024 | 18:30 | PKYFA - League Match | Scone Thistle 2011s | Luncarty YFC 2011's | Ref: Hugh Edens |
| Thu | 16-May-2024 | 15:30 | Schools - Dundee & District | St Paul's Roman Catholic Academy Boys U13 | St Johns RC High School Boys U13 | Ref: Nathan McDermott |
| Thu | 16-May-2024 | 10:30 | Schools - Dundee & District | St Paul's Roman Catholic Academy Boys U16 | Morgan Academy Boys U16 | |
| Fri | 17-May-2024 | 18:30 | Fife Football Development League - U14 | Crieff Juniors U14 (FFDL) | Bayside FC U14 | Ref: Robert W Mcdougall |
| Fri | 17-May-2024 | 18:30 | Friendly Match (Ref only) | FC Fair City Juniors U13 Whites (FFDL) | Broughty United YFC Boys U13 | Ref: Michael McQueen |
| Fri | 17-May-2024 | 12:00 | Schools - Dundee & District | Grove Academy Boys U14 | Braeview Academy Boys U14 | Ref: Brian Stewart |
| Fri | 17-May-2024 | 18:45 | DSMFL - George McArthur Cup (Final) | To be confirmed | To be confirmed | AR1: Gareth Ewing AR2: Kevin Higgins |
| Sat | 18-May-2024 | 09:30 | SWF - U14 League (9x9) | Brechin City Youths Girls U14 | Monifieth Ladies FC U14 | Ref: Cameron Chalmers |
| Sat | 18-May-2024 | 11:00 | SWF - League Cup | Crieff Girls U14 | To be Confirmed (F) | Ref: Simon Dexter |
| Sat | 18-May-2024 | 10:30 | SWF - League Cup | Dryburgh Girls U14 | Montrose Community FC Girls U14 | |
| Sat | 18-May-2024 | 10:00 | SWF - League Cup | Dundee East Community FC Girls U16 | East Fife Girls and Women's FC U14 | |
| Sat | 18-May-2024 | 10:00 | SWF - League Cup | Fair City Girls U14’s FC | Dunfermline FC Girls U14 (Whites) | |
| Sat | 18-May-2024 | 14:30 | ERSJFA - Midlands League | Forfar United JFC | Dundee North End JFC | |
| Sat | 18-May-2024 | 14:30 | ERSJFA - Midlands League | Forfar West End JFC | Scone Thistle JFC | |
| Sat | 18-May-2024 | 09:30 | SWF - League Cup | Jeanfield Swifts Girls U13 Jazz | Dunfermline FC Girls U14 (Reds) | Ref: Hugh Edens |
| Sat | 18-May-2024 | 11:30 | SWF - League Cup | Jeanfield Swifts Girls U14 (Jets) | Auchtermuchty Bellvue Colts | Ref: Hugh Edens |
| Sat | 18-May-2024 | 10:30 | SWF - League Cup | Jeanfield Swifts Girls U16 | Bayside Community Football Club U15 Girls | Ref: John Thornhill |
| Sat | 18-May-2024 | 14:30 | ERSJFA - Midlands League | Kirriemuir Thistle JFC | Dundee Downfield JFC | |
| Sat | 18-May-2024 | 14:30 | ERSJFA - Midlands League | Letham FC | Tayport JFC | |
| Sat | 18-May-2024 | 14:30 | ERSJFA - Quest Engineering Cup (Final Round) | Lochee United JFC | Dundee East Craigie JFC | AR1: Vikki A Robertson AR2: Joshua McCallum |
| Sat | 18-May-2024 | 10:30 | SWF - League Cup | Montrose Community FC Girls U16 | Dundee West FC Girls U16 Royals | |
| Sun | 19-May-2024 | 11:00 | PKYFA - League Match | Auchterarder YFC 2011's | Scone Thistle Blacks 2010s | Ref: Sandy McGregor |
| Sun | 19-May-2024 | 09:30 | PKYFA - League Match | Breadalbane and Strathtay Youth FC 2012s | Luncarty YFC 2012's | Ref: John Thornhill |
| Sun | 19-May-2024 | 12:00 | Scottish Women's Premier League 1 | Dundee United WFC | Motherwell WFC | AR1: Vikki A Robertson AR2: Jamie McCunnie |
| Sun | 19-May-2024 | 09:30 | PKYFA - League Match | Fair City Reds 2012’s | Crieff Juniors 2012's | Ref: David Skelly |
| Sun | 19-May-2024 | 11:00 | PKYFA - League Match | Jeanfield Swifts 2011's | Stanley 2011's | Ref: Ronald Dittrich |
| Sun | 19-May-2024 | 09:30 | PKYFA - League Match | Letham 2012’s | Pitfour FC 2012s | Ref: Kenneth J Laird |
| Sun | 19-May-2024 | 11:00 | PKYFA - League Match | Letham Sky Blues 2011's | FC Fair City 2011's | Ref: Kenneth J Laird |
| Sun | 19-May-2024 | 11:00 | PKYFA - League Match | Luncarty YFC 2011's | Crieff Juniors 2011's | Ref: Daniel Nedelcu |
| Sun | 19-May-2024 | 11:00 | PKYFA - League Match | Scone Thistle 2011s | Breadalbane and Strathtay Youth FC 2011s | Ref: Ivan Nsimbi |
| Sun | 19-May-2024 | 09:30 | PKYFA - League Match | Scone Thistle Blacks 2012s | Jeanfield Swifts whites 2012s | Ref: Ivan Nsimbi |
| Sun | 19-May-2024 | 13:00 | Scottish Women's Premier League 2 | St Johnstone WFC (Jeanfield Swifts) | Glasgow Women FC | AR2: Finlay Campbell |
| Sun | 19-May-2024 | 09:30 | PKYFA - League Match | Stanley 2011's (Venue: Dunkeld & Birnam AFC) | FC Fair City 2012s | Ref: Craig Harvey |
| Tue | 21-May-2024 | 16:00 | Schools - Dundee & District (WTR £) | Baldragon Academy u17s | Monifieth High School u17s | Ref: Brian Hutchison |
| Wed | 22-May-2024 | 18:30 | PKYFA - League Match | Breadalbane and Strathtay Youth FC 2010s | Scone Thistle 2011s | Ref: Simon Dexter |
| Wed | 22-May-2024 | 19:00 | ERSJFA - Midlands League | Carnoustie Panmure JFC | Letham FC | AR1: Vikki A Robertson AR2: Lewis Burns |
| Wed | 22-May-2024 | 18:30 | PKYFA - League Match | Crieff Juniors 2011's | Luncarty YFC 2011's | Ref: Robert W Mcdougall |
| Wed | 22-May-2024 | 19:00 | ERSJFA - Midlands League | Dundee Downfield JFC | Dundee St. James JFC | AR1: Hugh Edens AR2: Shaun Telford |
| Wed | 22-May-2024 | 18:30 | PKYFA - League Match | FC Fair City 2011's | Jeanfield Swifts 2011's | Ref: Sean McGregor |
| Wed | 22-May-2024 | 19:00 | Fife Football Development League - U14 | Luncarty YFC U14 (FFDL) | Letham Sports Club FC U14 (FFDL) | Ref: Craig Harvey |
| Wed | 22-May-2024 | 19:00 | ERSJFA - Midlands League | Scone Thistle JFC | Dundee Violet JFC | |
| Fri | 24-May-2024 | 19:00 | Fife Football Development League - U14 | Fair City Youth FC U14 (FFDL) | Templehall Utd U14's | Ref: Sandy McGregor |
| Sat | 25-May-2024 | 14:30 | ERSJFA - Midlands League | Dundee Downfield JFC | Dundee Violet JFC | AR1: Mark Findlay AR2: Finlay Campbell |
| Sat | 25-May-2024 | 11:00 | Fife Football Development League - U15 | Fair City Whites U15 (FFDL) | Kennoway Star Hearts FC | Ref: Sandy McGregor |
| Sun | 26-May-2024 | 11:00 | PKYFA Cup | Breadalbane and Strathtay Youth FC 2010s | Scone Thistle Development Blacks 2010s | Ref: Mark Craig AR1: John Thornhill AR2: Sandy McGregor |
| Sun | 26-May-2024 | 10:00 | Fife Football Development League - U14 | Crieff Juniors U14 (FFDL) | Templehall Utd U14's | Ref: Robert W Mcdougall |
| Sun | 26-May-2024 | 12:00 | Charity Match | To be Confirmed (M) | To be Confirmed (M) | |
| Tue | 28-May-2024 | 16:15 | Schools - Dundee & District | Harris Academy Boys U13 | St Paul's Roman Catholic Academy Boys U13 | |
| Wed | 29-May-2024 | 18:30 | PKYFA - League Match | Jeanfield Swifts 2011's | Scone Thistle 2011s | |
| Wed | 29-May-2024 | 18:45 | SWF - East Girls League | Panmure CFC Girls U13 | Jeanfield Swifts Girls U14 (Jets) | |
| Thu | 30-May-2024 | 14:00 | Schools - Angus (Finals) | Forfar Academy Boys Seniors | Montrose Academy Senior Boys | |
| Thu | 30-May-2024 | 19:00 | Fife Football Development League - U15 | Letham Sports Club FC U15 (FFDL) | Crossford United 09s | |
| Fri | 31-May-2024 | 19:00 | Fife Football Development League - U14 | Fair City Youth FC U14 (FFDL) | Inverkeithing United FC | Ref: Sean McGregor |
| Fri | 31-May-2024 | 18:45 | DSMFL - Shaun Kelly Cup (Final Round) | To be confirmed | To be confirmed | Ref: Steven Ferrier AR1: Kevin Riddell AR2: Craig Ritchie |
| Sun | 02-Jun-2024 | 11:00 | PKYFA - League Match | Breadalbane and Strathtay Youth FC 2010s | Crieff Juniors 2011's | |
| Sun | 02-Jun-2024 | 11:00 | PKYFA Cup | FC Fair City 2011's | Scone Thistle 2011s | Ref: Michael McQueen AR1: Liam McQueen AR2: Gary Lennie |
| Sun | 02-Jun-2024 | 14:00 | PKYFA Cup | Stanley 2011's | Letham Sky Blues 2011's | Ref: Kenneth J Laird AR1: Craig Harvey AR2: Sean McGregor |
| Wed | 05-Jun-2024 | 18:30 | PKYFA - League Match | Crieff Juniors 2011's | Stanley 2011's | Ref: Robert W Mcdougall |
| Sun | 09-Jun-2024 | 11:00 | PKYFA - League Match | Scone Thistle 2011s | Crieff Juniors 2011's | Ref: Sandy McGregor |
| Sun | 09-Jun-2024 | 11:00 | PKYFA - League Match | Stanley 2011's (Venue: Dunkeld & Birnam AFC) | Luncarty YFC 2011's | Ref: Craig Harvey |
| Mon | 10-Jun-2024 | 18:30 | Management Meeting | Management Committee | By Invite Only |