| 1 | Sat 21 Dec 2013 | 21-2 v WealdstoneWealdstone 2-1 Maidstone United | Ryman League Premier Division |
| 2 | Thu 26 Dec 2013 | 24-0 v MargateMaidstone United 4-0 Margate | Ryman League Premier Division |
| 3 | Sat 4 Jan 2014 | 21-1 v HendonMaidstone United 1-1 Hendon | Ryman League Premier Division |
| 4 | Sat 11 Jan 2014 | 21-0 v Grays AthleticGrays Athletic 0-1 Maidstone United | Ryman League Premier Division |
| 5 | Sat 18 Jan 2014 | 21-1 v Metropolitan PoliceMaidstone United 1-1 Metropolitan Police | Ryman League Premier Division |
| 6 | Tue 21 Jan 2014 | 21-4 v Thamesmead TownThamesmead Town 4-1 Maidstone United | Ryman League Premier Division |
| 7 | Sat 25 Jan 2014 | 27-2 v Hampton & Richmond BoroughMaidstone United 7-2 Hampton & Richmond Borough | Ryman League Premier Division |
| 8 | Tue 4 Feb 2014 | 31-0 v Burgess Hill TownMaidstone United 1-0 Burgess Hill Town | Robert Dyas League Cup Quarter Final |
| 9 | Sat 22 Feb 2014 | 155-0 v Wingate & FinchleyMaidstone United 5-0 Wingate & Finchley | Ryman League Premier Division |
| 10 | Tue 25 Feb 2014 | 146-0 v Grays AthleticMaidstone United 6-0 Grays Athletic | Robert Dyas League Cup Semi Final |
| 11 | Sat 8 Mar 2014 | 30-1 v LeistonLeiston 1-0 Maidstone United | Ryman League Premier Division |
| 12 | Sat 15 Mar 2014 | 104-3 v Dulwich HamletMaidstone United 4-3 Dulwich Hamlet | Ryman League Premier Division |
| 13 | Tue 18 Mar 2014 | 21-3 v East Thurrock UnitedEast Thurrock United 3-1 Maidstone United | Ryman League Premier Division |
| 14 | Sat 22 Mar 2014 | 160-1 v AFC HornchurchAFC Hornchurch 1-0 Maidstone United | Ryman League Premier Division |
| 15 | Sat 29 Mar 2014 | 141-1 v East Thurrock UnitedMaidstone United 1-1 East Thurrock United | Ryman League Premier Division |
| 16 | Sat 5 Apr 2014 | 72-1 v Bury TownBury Town 1-2 Maidstone United | Ryman League Premier Division |
| 17 | Sat 12 Apr 2014 | 61-1 v Enfield TownEnfield Town 1-1 Maidstone United | Ryman League Premier Division |
| 18 | Sat 19 Apr 2014 | 61-2 v Bognor Regis TownMaidstone United 1-2 Bognor Regis Town | Ryman League Premier Division |
| 19 | Mon 21 Apr 2014 | 62-1 v Metropolitan PoliceMetropolitan Police 1-2 Maidstone United | Ryman League Premier Division |
| 20 | Sat 26 Apr 2014 | 62-1 v Grays AthleticMaidstone United 2-1 Grays Athletic | Ryman League Premier Division |
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