The 2008/09 Nottinghamshire Senior League Senior Section Cup is a straight knockout tournament with the winner of the final crowned competition winners. Teams are drawn together randomly out of a hat with the winning teams each progressing through to the next stages. If any results are tied at ninety minutes then a further fifteen minutes each way will be played, if the result is still a tie after the extra time then a penalty shootout of five spot kicks each will be taken to decide the winner. If the score is still tied after the ten spot kicks then a sudden death shootout will take place until a winner is found.

The 2008/09 Reserve Section League Cup works as above but for the second string teams in the NSL. The competition was named the John Pye Reserve League Cup in 2005. Both competitions are played between January & May.

In the competition's debut year 17 Senior Division teams entered the Senior Section Cup with the first ever game (a preliminary round match) played between Cotgrave and Awsworth Villa which the home side won 4-2. Arnold Southbank, took advantage of some superb form in the second half of their season by reaching the final against an already crowned league champion Wollaton, the season's curtain drawer was played at Calverton Minors Welfare's impressive new ground with the champions proving too strong winning 3-1 en route to an impressive debut NSL season double. The Reserve Section was won by Attenborough Res in a tight game against Calverton Reserves at Cotgrave. The match, eventually going to extra time was won by Boro 3-1. Attenborough were back in finals action a year later with both of their sides represented. The sides first team losing to two late Anderson goals for Clifton in a tough encounter at Calverton, the Reserves also losing to Boots Reserves 2-0. In 2007 Wollaton Res reached the final after losing a quarter final match 5-2 against Clifton Reserves. Controversially Clifton were expelled for fielding an ineligible player, Barry Turner and Wollaton took their place against Boots at Hucknall Town FC's Watnall Road ground after a semi final win against Caribbean Cavaliers Reserves. Boots proving too strong winning 3-0, an Ibby Arsali double making him the first player to score in two (and consecutive) finals, he also scored a brace in the 2006 cup win. Caribbean Cavaliers, whose superb form from December onwards helped them reach the Senior Section final, Cav's beat Keyworth United 2-1 with all the goals coming before half time.  The 2008 cup for the first time included Division One teams in the Senior Section. The competition was extended to 20 teams but had the same outcome with Caribbean Cavaliers cruising to final victory over Linby CW 4-0. The Reserve Section was won a little less convincingly as Wollaton Reserves beat Basford Reserves in an epic battle on penalties at Hucknall Town FC. The first final to be won on penalties in the NSL's League Cup's short but sweet lifespan. Things were more straight forward in 2009, with both Senior and Reserve Section Cup's increasing in numbers, 23 sides participating in the Senior Cup and 20 in the John Pye Trophy. Greenwood Meadows Reserves in there debut year in the NSL going on to beat Keyworth United Res 1-0 in the final of Reserve Cup, Wollaton beating fellow NSL founder members Boots Athletic 2-1 in the Senior Division Final.