However, Bray Emmets, the leading side of the early 1900s, won Leinster and All-Ireland honours when they were playing in the Dublin Championship.

A League semi-final in frostbound 1947 came about in bizarre fashion: Wicklow were picked to represent an unfinished group in which some of the teams had not yet played.

After surviving the "long count" Meath went on to win the All-Ireland, and Wicklow lost their best player of the decade, John Timmons, to Dublin.

In 1986 they pulled off a huge upset beating newly crowned League champions Laois in the Leinster Quarter-final on a scorching hot June day in Aughrim by 2–10 to 1–9, Wicklow legend Kevin O'Brien scored 2–3 in that game.

A near thing against Meath, just off their four-match with Dublin in 1991 (Wicklow drew 0–12 to 1-9 and lost the replay by three points) heralded a great start to the 1990s.

But Wicklow's only championship wins since were against Longford and Westmeath, and a 1996 League quarter-final appearance against Donegal their nearest to a breakthrough.

The early part of the 2000s were very lean for Wicklow, with them winning very few championship matches; however, they did produce a number of competitive results and were unfortunate in several games.

In 2007 under Mick O'Dwyer they played Louth in the first round of the Leinster Championship, taking Louth to two replays before finally being beaten; however, later that year, they went on to win the 2007 Tommy Murphy Cup, defeating Antrim in dramatic fashion with a late Tommy Gill goal in extra-time,[1] securing the Wicklow senior footballers a second ever national trophy, and first ever win at Croke Park.

Again as they were a Division 4 team they were not permitted to enter the qualifiers, so they went on to try and defend the Tommy Murphy Cup but ultimately lost to Antrim in the final.

The 2009 Championship was one of the most memorable in Wicklow's history, they won their Leinster 1st-round game against Longford by 2–12 to 1-13 before narrowly losing to Westmeath in the next round by 0–16 to 1–10.

In 2010, Wicklow beat Carlow in the 1st round of the Leinster championship but again narrowly lost out in the Quarter-final, this time to Westmeath by a single point, 0–15 to 1-11 but unfortunately they were unable to repeat their historic 2009 Qualifier run losing out to Cavan in the 1st round, agonisingly by a single point again, 0–15 to 2–8.

[6] After Kelly resigned suddenly during the league campaign in early 2022, Alan Costello and Gary Duffy were appointed jointly as his successors.