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. In November 2013, he was named as
GAA/GPA Young Footballer of the Year. In November 2015, McCaffrey received the highest individual honour in the sport when he was named as
GAA/GPA 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". He travelled to
Ethiopia, then
Kenya,
Zambia,
Malawi and
Tanzania. McCaffrey played in
that year's All-Ireland final win but left the pitch early after sustaining what later proved to be an
anterior cruciate ligament injury. Interviewed the following day by journalists, McCaffrey reminded them: "This was the first time I've been on the pitch when the final whistle blew in an All-Ireland final. Incredible. It was so satisfying, such a relief." He was top scorer (1–3) from open play. He later described the drawn
2019 All-Ireland Senior Football Championship Final as the game that "broke me" but decided initially to remain when his former minor and under-21 manager
Dessie Farrell was appointed as Jim Gavin's successor. ==Honours==