1998–99 Dumbarton F.C. season
|Manager||Ian Wallace/Jimmy Brown|
|Stadium||Boghead Park, Dumbarton|
|Scottish League Division 3||4th|
|Scottish Cup||First Round|
|Scottish League Cup||First Round|
League: Paddy Flannery (17)|
All: Paddy Flannery (18)
|Highest home attendance||650|
|Lowest home attendance||230|
|Average home league attendance||391|
Season 1998–99 was the 115th football season in which Dumbarton competed at a Scottish national level, entering the Scottish Football League for the 93rd time, the Scottish Cup for the 104th time and the Scottish League Cup for the 52nd time.
Following three successive seasons of failure, Dumbarton produced what would be a marginally better league performance. Indeed, up until the beginning of April it was still technically possible for Dumbarton to have gained promotion, but in the end ran out of games. The season was improved by an end of season streak which saw 7 wins taken from the last 9 games, and eventually a 4th place was achieved. The winning run coincided with Ian Wallace's replacement by Jimmy Brown as manager, this following a suspension and subsequent internal investigation.
In the national cup competitions, it was a return to first round exits. In the Scottish Cup, Dumbarton lost to Livingston after a creditable drawn match.
In the League Cup, there was a disappointing first round defeat to Alloa Athletic.
Note that due to the lack of sponsorship, the Scottish Challenge Cup was not played.
Locally, in the Stirlingshire Cup, Dumbarton managed a draw from two ties and thus failed to reach the final.
All results are written with Dumbarton's score first.
|4 August 1998||Albion Rovers||H||2-0||McKinnon;Flannery||291|
|15 August 1998||Queen's Park||A||1-0||Sharp||656|
|22 August 1998||Stenhousemuir||H||0-2||378|
|29 August 1998||Berwick Rangers||H||0-0||303|
|5 September 1998||East Stirling||A||2-1||King;Robertson||217|
|12 September 1998||Brechin City||A||0-0||355|
|19 September 1998||Cowdenbeath||H||5-0||Sharp;Melvin(2);McKinnon;Flannery||348|
|26 September 1998||Montrose||A||1-1||Flannery||318|
|3 October 1998||Ross County||H||1-2||Flannery||538|
|10 October 1998||Queen's Park||H||1-0||Flannery||343|
|17 October 1998||Stenhousemuir||H||3-0||Glancy;Flannery;Mooney||456|
|24 October 1998||Berwick Rangers||H||1-3||Robertson||303|
|31 October 1998||East Stirling||H||2-2||Flannery;Robertson||309|
|7 November 1998||Cowdenbeath||A||2-0||Flannery(2)||228|
|14 November 1998||Brechin City||H||1-2||Flannery||357|
|25 November 1998||Montrose||H||0-2||240|
|28 November 1998||Ross County||A||0-2||1,759|
|12 December 1998||Albion Rovers||A||2-0||Flannery;Mooney||324|
|19 December 1998||Stenhousemuir||H||1-4||Wilson||283|
|16 January 1999||Montrose||A||2-4||Flannery(2)||326|
|26 January 1999||East Stirling||A||2-1||Brittain;Melvin||204|
|30 January 1999||Ross County||H||0-0||400|
|2 February 1999||Berwick Rangers||H||1-1||Flannery||242|
|13 February 1999||Brechin City||A||3-3||Grace;Mooney;Gow||360|
|27 February 1999||Queen's Park||A||1-1||Bradford||516|
|6 March 1999||East Stirling||H||0-2||246|
|9 March 1999||Albion Rovers||H||1-1||McKinnon||230|
|13 March 1999||Berwick Rangers||H||1-0||Flannery||321|
|20 March 1999||Ross County||A||2-1||Robertson;Bradford||2,374|
|3 April 1999||Montrose||H||2-1||Robertson(2)||541|
|5 April 1999||Cowdenbeath||H||6-1||Jack;Flannery;King(2);Smith;Stewart||650|
|10 April 1999||Cowdenbeath||A||1-2||Smith||245|
|17 April 1999||Brechin City||H||2-0||Robertson;Smith||562|
|24 April 1999||Stenhousemuir||H||2-0||Flannery;Mooney||629|
|1 May 1999||Queen's Park||H||0-1||762|
|8 May 1999||Albion Rovers||A||2-0||Robertson;Bruce||256|
|5 December 1998||1||Livingston||H||1-1||Flannery||530|
|8 December 1998||1R||Livingston||A||0-3||1,449|
Scottish League Cup
|1 August 1998||1||Alloa Athletic||H||0-4||352|
|23 July 1998||P||Stirling Albion||A||0-1|
|25 August 1998||P||Falkirk||H||2-2||Mooney;Robertson|
|25 July 1998||Ardeer Recreation||H||3-1||Flannery(2);Sharp|
|No.||Pos||Nat||Player||Total||Third Division||League Cup||Scottish Cup|
* The League match against Brechin City on 12 September marked Lee Sharp's 100th appearance for Dumbarton in all national competitions - the 112th Dumbarton player to reach this milestone.
* The League match against Cowdenbeath on 7 November marked Toby King's 100th appearance for Dumbarton in all national competitions - the 113th Dumbarton player to reach this milestone.
- Scottish Football League Review 1999-2000. The Scottish Football League. 2000.
- McAllister, Jim (2002). The Sons of the Rock - The Official History of Dumbarton Football Club. Dumbarton: J&J Robertson Printers.
- Litster, John. Record of Post-War Scottish League Players. Norwich: PM Publications.
- Derek Barnes (Dumbarton Football Club Historical Archive)
- Peter Dennison (Dumbarton Football Club Historical Archive)
- Paul Finnegan (Dumbarton Football Club Historical Archive)
- David Reid (Dumbarton Football Club Historical Archive)
- Barry Wilkinson (Dumbarton Football Club Historical Archive)
- Alan Brown (Dumbarton Football Club Historical Archive)
- Keith Miller (Dumbarton Football Club Historical Archive)
- Chris Smith (Dumbarton Football Club Historical Archive)
- Scottish Football Historical Archive