In
| Player | Team | Date | Fee |
|---|---|---|---|
| William Roche | Seacombe Swifts | 1 May 1899 | Free |
| Robert Gray | Partick Thistle | 27 May 1899 | £100 |
| Walter Abbott | Small Heath | 7 June 1899 | £250 |
| Ellis Green | Stalybridge Rovers | 31 January 1900 | £120 |
| Alex McDonald | Jarrow | 9 February 1900 | £80 |
| John Watson | Dundee | April 1900 | £50 |
| Joe Turner | Stoke | 17 April 1900 | £250 |
| Total (initial fees only): | £850 | ||
- John Watson (Dundee) – Transfer completed around 7th April 1900. Originally on trial.
Out
| Player | Team | Date | Fee |
|---|---|---|---|
| Edward Turner | Portsmouth | May 1899 | Undisclosed |
| Harry Clark | Portsmouth | May 1899 | Undisclosed |
| Harry Stringfellow | Portsmouth | May 1899 | Undisclosed |
| Jack Kirwan | Tottenham Hotspur | May 1899 | Undisclosed |
| Teddy Hughes | Tottenham Hotspur | May 1899 | Undisclosed |
| William Ball | Notts County | May 1899 | £50 |
| Billy Owen | Released | 1 May 1899 | |
| Charlie Harley | Released | 1 May 1899 | |
| Talbot Lewis | Released | 1 May 1899 | |
| Thomas Crompton | Released | 1 May 1899 | |
| Edgar Chadwick | Burnley | 30 May 1899 | £40 |
| John Tait Robertson | Rangers | 14 August 1899 | £250 |
| Laurie Bell | Bolton Wanderers | 26 August 1899 | Undisclosed |
| Total (initial fees only): | £340 | ||
- Billy Owen (Released) – Eventually retired.
- Charlie Harley (Released) – Eventually joined Berwick Rangers (Worcester) in November 1900.
- Talbot Lewis (Released) – Eventually joined Bristol City in May 1899.
- Thomas Crompton (Released) – Eventually retired due to injury.
- John Tait Robertson (Rangers) – John Tait Robertson may have already been sold to Southampton not as a co-ownership as stated.
| Income | £340 |
| Expenditure | £850 |
| Net Spend | +£510 |