He made a big impression in his time at East Kilbride, scoring two goals in eight league appearances and winning the club's Young Player of the Year award.

[10] In February 2004, Bryson scored in a 2–1 victory over Ross County in a Scottish Cup replay, which set up a quarter-final tie against Celtic, the team he supported as a boy.

[11] Bryson started against Celtic and thought he had scored after hitting the back of the net from a long-range strike, but this goal was controversially ruled out after the referee blew his whistle to award a free kick to Clyde.

In September 2005, he scored Clyde's equalising goal against Rangers in a Scottish League Cup tie at Ibrox Stadium, in a 5–2 extra time defeat.

[21] In the 2006–07 season, in October 2006, Bryson scored in a 3–1 victory over Greenock Morton in a Scottish Challenge Cup semi-final, which sent Clyde to their first major final in 48 years.

[24] Bryson's contract expired at the end of the season, and in January 2007, Billy Davies, then-manager of his future club Derby County, took him on a week's trial.

For his efforts, Bryson was named man of the match and won the plaudits of his manager Jim Jefferies, who said: "Craig's whole game was terrific and if he keeps playing like that we've got a real player on our hands.

Described variously as "stunning", "unstoppable", "sublime" and "a thunderbolt", he scored the second in a 2–0 win when he received a cross from Garry Hay and flicked the ball into the top corner.

[39][40][41] His next two goals were late winners in successive matches: on 4 October, in a 2–1 win at the Hearts he made a well-timed run into the box in the 82nd minute to collect a return pass from Donovan Simmonds and finish well into the bottom corner;[42][43][44] and then on 18 October, he scored the only goal in a 1–0 win at home to Motherwell, slipping the ball into the net at the far post in the 89th minute after a deflected shot-cum-cross from Jamie Hamill.

[45][46] Manager Jim Jefferies praised Bryson after the win over the Hearts, saying his late run into the box and finish were comparable to a move by Colin Cameron.

[51] Bryson ended the season with 4 league goals: a 90th minute consolation in a 2–1 defeat at home to Hearts on 28 November 2009;[52] Kilmarnock's 4th and the 7th in the match in a 4–4 draw with Dundee United on 30 January 2010 – a "stunning volley" that manager Jimmy Calderwood said was "fit to win any game";[53] the only goal in a 1–0 win over Falkirk on 10 February;[54] and a deflected cross that came off a Celtic defender in a 3–1 defeat at Celtic Park on 27 March.

[57][58][59] Hearts turned their attention to their former midfielder Paul Hartley, whose contract with English Championship club Bristol City was about to expire.

However, they dropped their interest in Hartley after he refused to distance himself from criticism of Hearts' majority shareholder Vladimir Romanov during his first stint with the club.

[60] Hearts thus turned their attention back to Bryson and gave Kilmarnock a final "take-it-or-leave-it" offer, which included a "significant sell-on clause" but not an increased transfer fee.

[68] Derby manager Nigel Clough called Bryson a "tremendous signing" and "a leader on and off the field" with "energy and ability in abundance".

[75] These goals cemented Bryson's place as Derby's third top scorer during the season, behind strikers Steve Davies and Theo Robinson.

[78] Bryson return three weeks earlier than expected as he started and scored in a 2–0 win at Bristol City however Nigel Clough stated he was not fully fit and was doubt for the next game.

[83] Ahead of the 2013–14 season, Bryson was expected to compete with Paul Coutts, Jeff Hendrick and Will Hughes for a central midfield role.

[85] After a 1–0 defeat at Nottingham Forest, with the club having won only once in the last six matches, having failed to win at home, and lying in 14th place, manager Nigel Clough was sacked.

[88] He recovered in time for the play-off final against Queens Park Rangers, but was named to the bench as the form of Will Hughes and Jeff Hendrick meant they kept their places.

[96] He played 90 minutes of the following match, a 1–0 FA Cup win against Southport on 3 January 2015, but then found himself on the sidelines for the rest of the season, behind Will Hughes, Jeff Hendrick and Omar Mascarell in the pecking order for the three central midfield places.

Having been top of the table in late February, a run of two wins from the last thirteen matches saw Derby finish eighth, a single point off the playoffs, and manager Steve McClaren sacked.

[98] However, he was ruled out for longer than first thought; six weeks later, new Derby manager Paul Clement reported that Bryson was still feeling some discomfort in his knee, which meant he was "finding some things difficult to do relating to shooting and long passing".

On the final day of the summer transfer window of 2017, Bryson joined fellow Championship side Cardiff City on a season-long loan deal.

[107] In August 2020 he was one of eight Aberdeen players who received a suspended three-match ban from the Scottish FA after they breached coronavirus-related restrictions by visiting a bar earlier in the month.

[113] In June 2022 following the end of his contract with St Johnstone, Bryson decided to go part-time and sign a one-year deal with Scottish League Two side Stenhousemuir.

[119] In 2013, Bryson was recalled to the senior squad for World Cup qualifiers against Belgium and Macedonia in September[120] and Croatia in October,[121] but did not get any match time.

[122] He was also called up for a post-season friendly against Nigeria, but while Derby teammates Chris Martin and Craig Forsyth made their debuts, Bryson did not come off the substitutes bench.

He put this improvement down to manager Steve McClaren: "he's changed the formation slightly and I have more freedom to get in the box and support Chris [Martin].

"[124] Scotland manager Gordon Strachan hailed the understanding between the two when he called them up for a friendly with Nigeria in May 2014: "When you look at the link-up between [Martin] and Bryson, I think it's 40-odd goals they've scored between them.