Leicestershire Leagues with divisional winners

Leicestershire Senior League
  Peacetime    Gresley Rovers
  Wartime    Loughborough Colleges
Coalville & District League
        
Loughborough & District Amateur Football Alliance
  Division One    Whitwick Holy Cross
  Division Two    Hathern United
  Division Three    Sileby Rangers

Non Leicestershire Leagues with Leicestershire based teams

The Football League
  Division Two    Leicester City
Kettering & District Amateur League
  Division One    Symingtons
Midland Amateur Alliance
  Division One    Old Loughburians

Leicestershire Cups with final score

Leicestershire & Rutland Senior Cup
  Quorn Methodists beat Leicester City Colts
Leicestershire County Junior Cup North
  Castle Donington Town beat Nailstone All Saints
Leicestershire County Junior Cup South
  Enderby Town beat Desford St. Marys
Loughborough Charity Cup
  Winner Ibstock Penistone Rovers
Rolleston Charity Cup
  Winner Ibstock Penistone Rovers
Automedia Printers Cobbin Trophy
  Shepshed Swifts  2  Whitwick Holy Cross  0

Non Leicestershire Cups

Name changes before the start of 1939/40.

None.

Name changes at the end of 1939/40.

None.

Mergers before the start of 1939/40.

None.

Mergers at the end of 1939/40.

None.

New teams for the start of 1939/40.

Anstey Methodists - Leicestershire Senior League
Cotton Sports - Loughborough & District Amateur Football Alliance
Pegsons United - Coalville & District League
Shepshed Town - Leicestershire Senior League
Sileby Rangers - Loughborough & District Amateur Football Alliance

Teams disappearing at the end of 1939/40.

Donisthorpe - Leicestershire Senior League
Hugglescote United - Leicestershire Senior League
Old Loughburians - Midland Amateur Alliance
Shepshed St. Winifreds - Loughborough & District Amateur Football Alliance
Sileby Old Boys - Loughborough & District Amateur Football Alliance