The Courtenay monument on the north wall of the chancel commemorates Sir Piers (Peter, Peirce) Courtenay, who died in 1552, and his wife Elizabeth Shilston, who died in 1605. The monument, with its kneeling figures above a tomb chest and flanking pilasters, was erected in 1607 by Thomas Clifford, Doctor of Divinity (1572–1634), son of Anne Clifford, one of the Courtenay daughters, and husband of Anne (or Amy), daughter of Hugh Staplehill of Trusham. The heraldry includes the Courtenay arms with a crescent for difference impaling Shilston, and above the pilasters the Clifford arms with a crescent charged with a mullet, impaling Staplehill, identifying the descent through which the Clifford family inherited Ugbrooke.
The inscription records that “Sir Peirce Courtenay married Elizabeth ye daughter of Robert Shilston who had issue VII children: Carers, Edward, James sonns; also daughters Katherine married to Kempthorn, Dorothy married to Corslinge, Anne married to Clifford, and Joan married to Eccmanne.” Behind the figures are biblical texts: Ecclus. 4, “Strive for ye truth unto death and defend justice for thy life, and ye Lord God shall fighte for thee,” and Psalm 112, “She hath distributed and given to the poore her rightousness remayneth for ever.” A short Greek text appears between them, now partly obscured. The monument retains traces of its original colour and is one of the most substantial post‑Reformation memorials in the church.
Sir Piers Courtenay was the son of Sir William Courtenay of Powderham and Margaret, daughter of Sir Richard Edgcumbe of Cotehele and Joan Tremayne, and grandson of Sir William Courtenay of Powderham and Cecily, daughter of John Cheney of Pinhoe and Elizabeth Hill. He married Elizabeth Shilston, heiress and daughter of Robert Shilston of Bridestowe. Their children included Edward, born 1556, who married Florence, daughter of Thomas Moore of Taunton and later wife of Humphry Walrond of Bovey. Edward and Florence had a daughter Catherine, wife of Josias Calmady of Wembury, parents of Sir Shilston Calmady. Edward is commemorated by a brass in St Margaret’s, Westminster, recording his death in 1556. Other children were Carew, who died young; James, who died without issue; Katherine, who married John Kempthorn alias Lea of Tunacombe, Cornwall; Dorothy, who married Jeffry Cowling of Cornwall; Anne, who married Anthony Clifford of Kingsteignton; and Joan, who married Richard Tremayne, Doctor of Divinity and Treasurer of Exeter, and died in 1595.
Sir Piers served as Sheriff of Devon and Lord High Treasurer and is credited with building Ugbrooke House in the parish. He died on 29 May 1552 at the age of 43 and was buried in the private chapel at Ugbrooke. His daughter Anne inherited Ugbrooke Park, establishing the long association of the Clifford family with the estate that continues to the present day. The 1607 monument in Chudleigh church, erected by her son Thomas Clifford, reflects this transfer of property and the consolidation of the Clifford presence in the district.