Season 44
| Pre-Season Auction A | Deadline: Saturday March 25th 06:00 PM |
| Auction 1: 10 players available Trades window opens No coaching | Trading window opens for the season |
| Pre-Season Auction B | Deadline: Saturday April 1st 06:00 PM |
| Auction 2: 10 players available Trades allowed No coaching | |
| Session 1 | Deadline: Saturday April 8th 06:00 PM |
| Match 1: FA Cup Round 1 (draw results in a replay) Match 2: AP Cup (Group) Match 3: AP Cup (Group) Auction 3: 8 players available Session trade window closes 48 hours prior to deadline Coaching allowed Captains MUST be selected by this deadline. | Start of matches |
| Session 2 | Deadline: Saturday April 15th 06:00 PM |
| Match 4: League Round 1 Match 5: League Round 2 Match 6: FA Cup Round 1 Replay (draw results in a PK shootout) Match 7: AP Cup (Group) Auction 4: 8 players available Session trade window closes 48 hours prior to deadline Coaching allowed | |
| Session 3 | Deadline: Saturday April 22nd 06:00 PM |
| Match 8: League Round 3 Match 9: League Round 4 Match 10: FA Cup Round 2 (draw results in a replay) Match 11: FA Shield Round 1 (draw results in extra time then PK shootout) Auction 5: 8 players available Session trade window closes 48 hours prior to deadline Coaching allowed | |
| Session 4 | Deadline: Saturday April 29th 06:00 PM |
| Match 12: League Round 5 Match 13: League Round 6 Match 14: FA Cup Round 2 Replay (draw results in a PK shootout) Match 15: AP Cup Round 2 (draw results in extra time then PK shootout) Auction 6: 8 players available Session trade window closes 48 hours prior to deadline Coaching allowed | |
| Session 5 | Deadline: Saturday May 6th 06:00 PM |
| Match 16: League Round 7 Match 17: League Round 8 Match 18: FA Cup Quarterfinals (draw results in a replay) Match 19: AP Cup Quarterfinals (draw results in extra time then PK shootout) Auction 7: 8 players available Session trade window closes 48 hours prior to deadline Coaching allowed | |
| Session 6 | Deadline: Saturday May 13th 06:00 PM |
| Match 20: League Round 9 Match 21: League Round 10 Match 22: FA Cup Quarterfinals Replay (draw results in extra time then PK shootout) Match 23: FA Shield Quarterfinals (draw results in extra time then PK shootout) Match 24: Youth Cup Round 1 (draw results in PK shootout) Auction 8: 8 players available Session trade window closes 48 hours prior to deadline Coaching allowed | Youth Cup opens (must have 8 SBY + APP players on roster) Final auction of the season |
| Session 7 | Deadline: Saturday May 20th 06:00 PM |
| Match 25: League Round 11 Match 26: League Round 12 Match 27: AP Cup Semifinals (draw results in extra time then PK shootout) Match 28: Youth Cup Round 2 (draw results in PK shootout) Session trade window closes 48 hours prior to deadline Coaching allowed | |
| Session 8 | Deadline: Saturday May 27th 06:00 PM |
| Match 29: League Round 13 Match 30: League Round 14 Match 31: FA Cup Semifinals (draw results in extra time then PK shootout) Match 32: FA Shield Semifinals (draw results in extra time then PK shootout) Match 33: Youth Cup Quarterfinals (draw results in PK shootout) Session trade window closes for the season 48 hours prior to deadline Coaching allowed Taxation on bank accounts 3500k and above occurs after money earned in session 8 | Transfer Deadline (no trades allowed after this deadline) Non League Sales Deadline (no sales allowed after this deadline) |
| Session 9 | Deadline: Saturday June 3rd 06:00 PM |
| Match 34: League Round 15 Match 35: League Round 16 Match 36: AP Cup Final (draw results in extra time then PK shootout) Match 37: Youth Cup Semifinals (draw results in PK shootout) Session trade window closes 48 hours prior to deadline Coaching allowed No trading or non-league sales allowed | AP Cup Final |
| Session 10 | Deadline: Saturday June 10th 06:00 PM |
| Match 38: League Round 17 Match 39: League Round 18 Match 40: FA Cup Final (draw results in extra time then PK shootout) Match 41: FA Shield Final (draw results in extra time then PK shootout) Match 42: Youth Cup Final (draw results in PK shootout) Backroom boys must be converted prior to deadline if they would retire after aging Coaching allowed No trading or non-league sales allowed | Final session of Season 44 FA Cup Final FA Shield Final Youth Cup Final |