Coalville Town out in the Third Qualifying Round, Leicester City lose to Chelsea in the Quarter Finals.
Extra Prelim Round > Prelim Round > First Round Qual > Second Round Qual > Third Round Qual > Third Round > Fourth Round > Fifth Round > Quarter Finals
Leicestershire Entries – 16 Teams
Football League
Leicester City.
Southern League
Barwell and Coalville Town.
Northern Premier League
Anstey Nomads, Harborough Town, Hinckley LRFC, Loughborough Dynamo, Quorn and Shepshed Dynamo.
United Counties League
Ashby Ivanhoe, Aylestone Park, GNG Oadby Town, Leicester Nirvana, Loughborough Students, Lutterworth Town and Melton Town.
Extra Preliminary Round
| 5th August 2023 | | |
| Ashby Ivanhoe | 3 – 0 | Deeping Rangers |
| Boston Town | 0 – 0 | Anstey Nomads |
| Bugbrooke St. Michaels | 2 – 3 | Hinckley LRFC |
| Cleethorpes Town | 1 – 1 | Loughborough Dynamo |
| GNG Oadby Town | 1 – 3 | Bottesford Town |
| Grantham Town | 1 – 1 | Loughborough Students |
| Lutterworth Town | 0 – 3 | Lincoln United |
| Quorn | 1 – 1 | Carlton Town |
| Rossington Main | 4 – 1 | Leicester Nirvana |
| Sherwood Colliery | 2 – 2 | Aylestone Park |
| Winterton Rangers | 2 – 4 | Melton Town |
| 8th August 2023 | | |
| Sleaford Town | 0 – 2 | Shepshed Dynamo |
Replays
| 8th August 2023 | | |
| Anstey Nomads | 2 – 2
(5 – 3 pens) | Boston Town |
| Aylestone Park | 1 – 2 | Sherwood Colliery |
| Carlton Town | 2 – 0 | Quorn |
| Loughborough Dynamo | 0 – 2 | Cleethorpes Town |
| Loughborough Students | 0 – 1 | Grantham Town |
Byes: Barwell, Coalville Town and Harborough Town.
Preliminary Round
| 19th August 2023 | | |
| Anstey Nomads | 2 – 1 | Eastwood Community |
| Ashby Ivanhoe | 1 – 0 | Rossington Main |
| Grimsby Borough | 4 – 2 | Melton Town |
| Hinckley LRFC | 2 – 1 | Bewdley Town |
| Newark & Sherwood United | 0 – 4 | Harborough Town |
| Spalding United | 1 – 1 | Shepshed Dynamo |
Replays
| 22nd August 2023 | | |
| Shepshed Dynamo | 2 – 3 | Spalding United |
Byes: Barwell and Coalville Town.
First Round Qualifying
| 2nd September 2023 | | |
| AFC Telford United | 0 – 1 | Coalville Town |
| Anstey Nomads | 3 – 0 | Hanley Town |
| Ashby Ivanhoe | 0 – 2 | Bromsgrove Sporting |
| Cleethorpes Town | 2 – 1 | Hinckley LRFC |
| Harborough Town | 3 – 1 | Stamford AFC |
| Rugby Town | 0 – 2 | Barwell |
Second Round Qualifying
| 16th September 2023 | | |
| Barwell | 1 – 2 | Bromsgrove Sporting |
| Coalville Town | 2 – 1 | Stafford Rangers |
| Hereford | 2 – 0 | Anstey Nomads |
| Tamworth | 2 – 1 | Harborough Town |
Third Round Qualifying
| 30th September 2023 | | |
| Coalville Town | 0 – 2 | Tamworth |
Third Round
| 6th January 2024 | | |
| Millwall | 2 – 3 | Leicester City |
Fourth Round
| 27th January 2024 | | |
| Leicester City | 3 – 0 | Birmingham City |
Fifth Round
| 27th February 2024 | | |
| AFC Bournemouth | 0 – 1 | Leicester City |
Quarter Finals
| 17th March 2024 | | |
| Chelsea | 4 – 2 | Leicester City |
