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McCaffrey won the man of the match award in the drawn 2019 All-Ireland Senior Football Championship Final as well; a second consecutive award, "RTÉ veterans" were reported to be finding it difficult to recall such an occurrence ever before. He was top scorer (1–3) from open play. This compared with the 3–14 from his previous 38 championship games. The three points were also a classic hat-trick, sent over with fist and both feet. Defensively, he forced eight turnovers of possession.

McCaffrey returned for Dublin against Longford as a substitute in June 2018. Another substitute appearance in the Leinster final against Laois followed, seeing him make two goal chances by himself. However, he did not find the net in that game.

He is a former self-admitted "horrific tackler" but the 2018 All-Ireland Senior Football Championship Final proved to be when he "figured out I'm actually a defender as opposed to some loose attacking player". His dispossession of Mattie Donnelly during injury time of that game offered evidence of this.

McCaffrey was named Man of the Match after his team's 2018 final victory. While being interviewed by Lyster for The Sunday Game highlights programme, a leak through the ceiling of the Gibson Hotel caused Lyster, McCaffrey and GAA President John Horan to be drenched in water live on air.

McCaffrey missed the 2016 All-Ireland Senior Football Championship due his travels abroad. He travelled to Ethiopia, then Kenya, Zambia, Malawi and Tanzania.

In December 2016, McCaffrey confirmed that he would be available again for selection in 2017.

In November 2015, McCaffrey received the highest individual honour in the sport when he was named as All Stars Footballer of the Year. He did so in spite of contracting food poisoning "in around the Thursday" before the 2015 All-Ireland Senior Football Championship Final, which left him unable to finish the game. "I couldn't keep any food or water down so I got a drip to stay hydrated. But that was actually great at the time because it completely distracted from the build-up to a final ... all you were worried about is, 'Am I going to be okay?' You're no thinking about the occasion itself. And then thankfully I pulled through and performed okay for the 50 minutes that I lasted".

In April 2013, McCaffrey won a National Football League winners' medal as Dublin defeated Tyrone by 0–18 to 0–17 to win the 2013 National Football League. He made his championship debut against Westmeath in the 2013 Leinster Senior Football Championship. He scored a solo goal in the 2013 All-Ireland quarter-final against Cork. Still teenaged, he played in the 2013 All-Ireland Senior Football Championship Final, the first such final he would play in. McCaffrey, who was substituted at half-time, recalled how he "got roasted by Kevin McLoughlin". He played twice and netted for Ireland against Australia in the 2013 International Rules Series. In November 2013, he was named as All Stars Young Footballer of the Year.

Jack McCaffrey (born 19 October 1993) is a Gaelic footballer for the Dublin senior football team and plays for his club Clontarf.